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  • 50-78-2 Structure
  • Basic information

    1. Product Name: Acetylsalicylic acid
    2. Synonyms: O-ACETYLSALICYLIC ACID;O-ACETOXYBENZOIC ACID;ACETICYL;ACETOXYBENZOIC ACID;ACETYLSALICYLIC ACID;ACETYSALICYLIC ACID;ACETYLSALICYLIC ACID IMPURITY D;ALKENYL SUCCINIC ANHYDRIDES
    3. CAS NO:50-78-2
    4. Molecular Formula: C9H8O4
    5. Molecular Weight: 180.16
    6. EINECS: 200-064-1
    7. Product Categories: Pharmaceutical;Aromatics Compounds;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Lipid signaling;Anti-Allergic Agents, Antibiotic;Isotope;LOPROX
    8. Mol File: 50-78-2.mol
    9. Article Data: 112
  • Chemical Properties

    1. Melting Point: 134-136 °C(lit.)
    2. Boiling Point: 272.96°C (rough estimate)
    3. Flash Point: 250 °C
    4. Appearance: white/crystalline
    5. Density: 1.35
    6. Vapor Pressure: 0.000124mmHg at 25°C
    7. Refractive Index: 1.4500 (estimate)
    8. Storage Temp.: Store at RT.
    9. Solubility: H2O: 10 mg/mL at 37 °C
    10. PKA: 3.5(at 25℃)
    11. Water Solubility: 3.3 g/L (20 ºC)
    12. Stability: Stable. Keep dry. Incompatible with strong oxidizing agents, strong bases, strong acids, various other compounds such as iodides
    13. Merck: 14,851
    14. BRN: 779271
    15. CAS DataBase Reference: Acetylsalicylic acid(CAS DataBase Reference)
    16. NIST Chemistry Reference: Acetylsalicylic acid(50-78-2)
    17. EPA Substance Registry System: Acetylsalicylic acid(50-78-2)
  • Safety Data

    1. Hazard Codes: Xn
    2. Statements: 22-36/37/38
    3. Safety Statements: 26-36/37/39
    4. RIDADR: UN 1851
    5. WGK Germany: 1
    6. RTECS: VO0700000
    7. TSCA: Yes
    8. HazardClass: 6.1
    9. PackingGroup: III
    10. Hazardous Substances Data: 50-78-2(Hazardous Substances Data)

50-78-2 Usage

Description

Acetylsalicylic acid, commonly known as aspirin or ASA, is a white crystalline powder and a member of the benzoic acid class. It is a salicylate drug that serves as a non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity. Aspirin is the most widely used medication globally, known for its analgesic, antipyretic, and anti-inflammatory properties.

Uses

1. Used in Pharmaceutical Industry:
Acetylsalicylic acid is used as an analgesic for mild to moderate pain, an antipyretic to reduce fever, and an anti-inflammatory medication. It is also used to inhibit platelet aggregation, making it useful in the prevention of arterial and venous thrombosis.
2. Used in Anticancer Applications:
Although not explicitly mentioned in the provided materials, aspirin has been shown to be effective at preventing certain types of cancer, particularly colorectal cancer.
3. Used in Chemical Synthesis:
Acetylsalicylic acid serves as the raw material for rodenticide intermediates, such as 4-hydroxycoumarin.
4. Used in Construction and Automotive Industry:
Acetylsalicylic acid is used in the production of outdoor structural members and equipment parts exposed to highlights, such as automobile bodies, agricultural machinery parts, meters, electric lamps, and road markings.
5. Used in Antifungal Applications:
The materials do not provide specific details on the use of aspirin as an antifungal agent, but it is listed as one of its uses.
6. Used in Drug Delivery Systems:
Acetylsalicylic acid is used as an intermediate in the synthesis of other medicines, including Axepim Cephalosporin antibiotic.
7. Used in the Synthesis of Aspirin:
The synthesis of aspirin is classified as an esterification reaction, where salicylic acid is treated with acetic anhydride to produce aspirin and acetic acid.

What’s acetylsalicylic acid?

Acetylsalicylic acid, also known as aspirin, is an analgesic-antipyretic medicine made by salicylic acid interacting with acetic anhydride. It is a white crystalline powder, odorless, stable in dry air. It will be slowly hydrolyzed to be salicylic acid and acetic acid in moist air, and aqueous solution has acidic reaction. Slightly soluble in water, soluble in ethanol, ethyl ether, chloroform, sodium hydroxide solution and sodium carbonate solution. Acetylsalicylic acid has antipyretic analgesic, anti-inflammatory and anti-rheumatism effect, that’s why it is often used for fever, headache, muscle pain, neuralgia, rheumatic fever, acute rheumatic arthritis, gout, etc.; also it has antiplatelet aggregation effect, and can be used for prevention of arterial thrombosis, atherosclerosis, transient cerebral ischemia and myocardial infarction; in addition, acetylsalicylic acid also can be used in the treatment of biliary tract roundworm disease and athlete's foot. Pharmacological actions Acetylsalicylic acid is one of the traditional antipyretic analgesics, as well as the role of platelet aggregation. Acetylsalicylic acid in the body has the characteristics of the antithrombotic, can reduce the formation of obstructive blood clots in surrounding arteries, and inhibit release of platelet response and endogenous ADP, 5-HT, etc., therefore to inhibit second phase other than the first phase of platelet aggregation. The mechanism of action of acetylsalicylic acid is to make platelets cyclooxygenase acetylation, thus inhibiting the formation of ring peroxide, and TXA2 formation is also reduced as well. At the mean time make the platelet membrane protein acetylation, and inhibit platelet membrane enzyme, which helps to inhibit platelet function. As the cyclooxygenase is inhibited, it impacts blood vessel wall synthesized to be PGI2, the platelet TXA2 synthetic enzymes also to be inhibited; so it would impact formation of both TXA2 and PGI2 when it is large doses. Suitable for ischemic heart disease, after percutaneous transluminal coronary angioplasty or coronary artery bypass grafting, prevent transient ischemic stroke, myocardial infarction and reduce the incidence of arrhythmia. The above information is edited by the lookchem He Liao Pu.

Chemical property

This product is a white crystalline, with melting point 138~140 ℃, insoluble in water, soluble in alcohol, ether, etc.

How Aspirin is used in Ischemic Stroke therapy

In the therapy of Ischemic Stroke, 50 to 325 mg/day started between 24 and 48 hours after completion of alteplase has also been shown to reduce long-term death and disability. Aspirin, clopidogrel, and extended-release dipyridamole plus aspirin are all considered first-line antiplatelet agents. The combination of aspirin and clopidogrel can only be recommended in patients with ischemic stroke and a recent history of myocardial infarction or coronary stent placement and then only with ultra-low-dose aspirin to minimize bleeding risk.

Production method

Acetylsalicylic acid: add acetic anhydride (feeding ratio is 0.7889 times of the total salicylic acid) in reaction vessel, and then add two thirds of salicylic acid, stir it and temperature rises. React 40-60min in 81-82℃. Cool it to 81-82 ℃ and keep the temperature for 2h. When free salicylic acid is qualified, cool it to 13 ℃, precipitation crystallization, rejection filter, dry it in 65-70℃ air flow, then we get acetylsalicylic acid.

Toxicity grading

High toxic

Acute toxicity

Oral-rat LD50: 200 mg/kg; Oral-mice LD50: 250 mg/kg

Flammable hazardous characteristics

Flammable in fire; irritant gas would be decomposed out when heated.

Handling and storage characteristics

Warehouse needs to be ventiIative and dry with low temperature; separate it from oxidant and food additives.

Fire extinguishing agent

Water fog, foam, carbon dioxide, sandy soil.

Occupational standard

TWA 5 mg/m3

Originator

Entab,Mayrand,US,1982

History

The use of Acetylsalicylic acid goes back thousands of years, and there are numerous accounts of the medicinal properties of plants from the Salix (willow) and Myrtaceae (Myrtle) families. Writings from ancient civilizations indicate the use of willow bark in Mesopotamia and myrtle leaves in Egypt as medicines existing several thousand years b.c.e. Hippocrates (460–377 b.c.e. ) and the ancient Greeks used powdered willow bark and leaves to reduce fever (antipyretic) and as a pain reliever (analgesic). Willow and oil of wintergreen was used as medications by native Americans. The chemical responsible for the medicinal properties in willow and oil of wintergreen are forms of salicylates, a general name to describe compounds containing the general structure of salicylic acid. Willows (genus Salix) contain salicin and oil of wintergreen contains methyl salicylate. Although the use of willow bark and oil of wintergreen as an accepted antipyretic and analgesic has occurred for at least 2,000 years, by the 19th century medicines were starting to be synthesized in chemical laboratories.

Indications

Acetylsalicylic acid is available as capsules, tablets, enteric-coated tablets (Ecotrin), timed-release tablets (ZORprin), buffered tablets (Ascriptin, Bufferin), and as rectal suppositories. Sodium salicylate is available generically. Other salicylates include choline salicylate (Arthropan), choline magnesium trisalicylate (Trilisate), and magnesium salicylate (Momentum).

Manufacturing Process

As described in US Patent 2,731,492, a glass-lined reactor of 1,500 gallons capacity, fitted with a water-cooled reflux condenser, thermometers with automatic temperature registers and an efficient agitator, is employed. To start the process, a mother liquor is made by dissolving 1,532 kg of acetic anhydride (15 mols) in 1,200 kg of toluene. To this mother liquor, add 1,382 kg of salicylic acid (10 mols), heat the reaction mixture under an efficient reflux condenser, to 88-92°C and maintain within this temperature range for 20 hours. The reaction mixture is now transferred to aluminum cooling tanks, and is allowed to cool slowly, over a period of 3 to 4 days, to a terminal temperature of 15-25°C (room temperature). The acetylsalicylic acid precipitates as large, regular crystals. The mother liquor is now filtered or centrifuged from the precipitated acetylsalicylic acid and the filter cake is pressed or centrifuged as free of mother liquor as possible. The crystals are washed with distilled water until completely free of acetic acid, pressed or centrifuged as dry as possible and the filter cake is then dried in a current of warm air at a temperature of 60-70°C.The filtrate from this first batch will comprise a solution of 180 to 270 kg of unprecipitated acetylsalicylic acid (1.0 to 1.5 mols), 510 kg of acetic anhydride (5.0 mols), 600 kg of acetic acid (10.0 mols) (obtained as a byproduct in the acetylation step) and 1,200 kg of the diluent toluene. Into this filtrate, at a temperature of 15° to 25°C, ketene gas is now passed through a sparger tube or diffuser plate, with good agitation, until a weight increase of 420.5 kg of ketene (10 mols) occurs. The reaction mixture will now contain 180-270 kg of unprecipitated acetylsalicylic acid (1.0-1.5 mols) and 1,532 kg of acetic anhydride (15 mols) in 1,200 kg of toluene. This mother liquor is recycled to the first step of the process for reaction with another batch of 1,382 kg of salicylic acid. On recirculating the mother liquor, the yield of pure acetylsalicylic acid is 1,780 to 1,795 kg per batch.

World Health Organization (WHO)

Acetylsalicylic acid, a nonsteroidal anti-inflammatory, analgesic and antipyretic agent, was introduced into medicine in 1899 and has since been widely available in over-the-counter preparations. Recent studies carried out in the USA have shown an association between acetylsalicylic acid consumption in children and the development of Reye's syndrome (a rare condition characterized by a combination of encephalopathy and liver disorder and usually preceded by an acute viral illness, such as influenza, diarrhoea, or chickenpox). Many drug regulatory authorities have acted to caution against the use of the drug in children and young adults with febrile conditions. Even within this group the risk of exposure is remote and has been estimated to be of the order of 1.5 per million. This warning also concerns products containing other salicylates. The new indication of acetylsalicylic acid - prophylaxis of myocardial infarction due to its antithrombotic effect - requires loneterm use and may lead to serious adverse reactions, including cerebral haemorrhage. Acetylsalicylic acid retains a valuable place in medicine and remains in the WHO Model List of Essential Drugs.

Biological Functions

Acetylsalicylic acid is one of the most important NSAIDs because it decreases pain at predominantly peripheral sites with little cortical interaction and thus has few CNS effects. The prototypical COX-2 inhibitors are celecoxib (Celebrex) and its chemical cousin, rofecoxib (Vioxx). In addition to a role in inflammatory processes,COX-2 seems to play a role in colon cancer and Alzheimer’s disease, providing potential additional uses for COX-2-selective drugs.

Acquired resistance

Acetylsalicylic acid is rapidly absorbed in the stomach and quickly degraded by plasma cholinesterases (half-life, 15–20 min). A once-daily dose of 160 mg of aspirin, which is much lower than dosages needed for its anti-inflammatory/analgesic actions, is sufficient to completely inactivate platelet COX-1 irreversibly. Higher doses of aspirin only contribute to its side effects, especially internal bleeding and upper gastrointestinal irritations.

Air & Water Reactions

Slowly hydrolyzes in moist air. Has been involved in dust cloud explosions. Water insoluble. Solution in water is acid to methyl red indicator.

Reactivity Profile

The active ingredient in common aspirin. Incompatible with oxidizers and strong acids. Also incompatible with strong bases. May react with water or nucleophiles (e.g. amines and hydroxy groups). May also react with acetanilide, amidopyrine, phenazone, hexamine, iron salts, phenobarbitone sodium, quinine salts, potassium and sodium iodides, alkali hydroxides, carbonates, stearates and paracetanol.

Hazard

An allergen; may cause local bleeding espe- cially of the gums; 10-g dose may be fatal. May cause excessive biosynthesis of prostaglandins. Dust dispersed in air is serious explosion risk. Skin and eye irritant.

Fire Hazard

Acetylsalicylic acid is combustible.

Biochem/physiol Actions

Blocks the production of prostaglandins by inhibiting cyclooxygenase (prostaglandin H synthase), with greater selectivity toward the COX-1 isoform. The antithrombotic effect is due to the inhibition of COX-1 in platelets that blocks thromboxane production and platelet aggregation. Chemopreventive against colorectal and other solid tumors.

Mechanism of action

Discovery of the mechanismIn 1971, British pharmacologist John Robert Vane, then employed by the Royal College of Surgeons in London, showed Acetylsalicylic acid?suppressed the production of prostaglandins and thromboxanes.Suppression of prostaglandins and thromboxanesAcetylsalicylic acid's ability to suppress the production of prostaglandins and thromboxanes is due to its irreversible inactivation of the cyclo oxygenase (PTGS) enzyme required for prostaglandin and thromboxane synthesis. Acetylsalicylic acid?acts as an acetylating agent where an acetyl group is covalently attached to a serine residue in the active site of the PTGS enzyme.COX-1 and COX-2 inhibitionThere are at least two different types of cyclooxygenase: COX-1 and COX-2. Acetylsalicylic acid?irreversibly inhibits COX-1 and modifies the enzymatic activity of COX-2. COX-2 normally produces prostanoids, most of which are proinflammatory. Acetylsalicylic acid-modified PTGS2 produces lipoxins, most of which are anti-inflammatory.Additional mechanismsAcetylsalicylic acid?has been shown to have at least three additional modes of action. It uncouples oxidative phosphorylation in cartilaginous (and hepatic) mitochondria, by diffusing from the inner membrane space as a proton carrier back into the mitochondrial matrix, where it ionizes once again to release protons . In short, Acetylsalicylic acid?buffers and transports the protons. When high doses of Acetylsalicylic acid?are given, it may actually cause fever, owing to the heat released from the electron transport chain, as opposed to the antipyretic action of Acetylsalicylic acid?seen with lower doses.Hypothalamic - pituitary - adrenal activityAcetylsalicylic acid, like other medications affecting prostaglandin synthesis, has profound effects on the pituitary gland, which indirectly affects a number of other hormones and physiological functions.

Pharmacology

Acetylsalicylic acid is a weak acid, and very little of it is ionized in the stomach after oral administration. Acetylsalicylic acid is poorly soluble in the acidic conditions of the stomach, which can delay absorption of high doses for eight to 24 hours. The increased pH and larger surface area of the small intestine causes aspirin to be absorbed rapidly there, which in turn allows more of the salicylate to dissolve. Owing to the issue of solubility, however, aspirin is absorbed much more slowly during overdose, and plasma concentrations can continue to rise for up to 24 hours after ingestion.

Pharmacology

Although Acetylsalicylic acid?itself is pharmacologically active, it is rapidly hydrolyzed to salicylic acid after its absorption, and it is the salicylate anion that accounts for most of the anti-inflammatory activity of the drug. The superior analgesic activity of Acetylsalicylic acid?compared with sodium salicylate implies that Acetylsalicylic acid?has an intrinsic activity that is not totally explainable by its conversion to salicylic acid. Acetylsalicylic acid?inhibits COX-1 to a much greater extent than COX-2; sodium salicylate is more selective for COX-1. This, combined with the ability of Acetylsalicylic acid?to acetylate proteins, might account for some of the therapeutic and toxicological differences between Acetylsalicylic acid?and the other salicylates.The binding of salicylic acid to plasma proteins varies with its plasma concentrations. At serum salicylic acid concentrations of less than 100 μg/mL, 90 to 95% is protein bound; at 100 to 400 μg/mL, 70 to 85% is protein bound; and at concentrations greater than 400 μg/mL, 20 to 60% is protein bound. The plasma concentration of salicylate that is associated with antiinflammatory activity (200–300 μg/mL) is about six times that needed to produce analgesia. At these higher concentrations, salicylate metabolism is reduced, resulting in a longer half-life for the drug. This reaction is a consequence of the saturable enzyme systems that metabolize salicylates. The plasma half-life for salicylate has been estimated to be 3 to 6 hours at the lower (analgesic) dosage and 15 to 30 hours at the higher (antiinflammatory) dosages.The rate of hydrolysis of Acetylsalicylic acid?to salicylic acid is not dose limited, and no differences in the absorption of Acetylsalicylic acid?have been observed between arthritic patients and normal individuals.

Clinical Use

Acetylsalicylic acid?is used in the treatment of a number of conditions, including fever, pain, rheumatic fever, and inflammatory diseases, such as rheumatoid arthritis, pericarditis, and Kawasaki disease.PainAsprin 325 MG for pain In most cases, Acetylsalicylic acid?is considered inferior to ibuprofen for the alleviation of pain, because Acetylsalicylic acid?is more likely to cause gastrointestinal bleeding . Acetylsalicylic acid?is generally ineffective for those pains caused by muscle cramps, bloating, gastric distension, or acute skin irritation.HeadacheAcetylsalicylic acid, either by itself or in combined formulation, effectively treats some types of headache, but its efficacy may be questionable for others.Acetylsalicylic acid?or other overthe- counter analgesics are widely recognized as effective for the treatment of tension headache. Acetylsalicylic acid, especially as a component of an acetaminophen/Acetylsalicylic acid/caffeine formulation (e.g., Excedrin Migraine), is considered a first - line therapy in the treatment of migraine, and comparable to lower doses of sumatriptan.FeverLike its ability to control pain, Acetylsalicylic acid's ability to control fever is due to its action on the prostaglandin system through its irreversible inhibition of COX .Heart attacks and strokesFor a subset of the population, Acetylsalicylic acid?may help prevent heart attacks and strokes. In lower doses, Acetylsalicylic acid?has been known to prevent the progression of existing cardiovascular disease, and reduce the frequency of these events for those with a history of them . ( This is known as secondary prevention.)Post-surgeryAfter percutaneous coronary interventions (PCIs), such as the placement of a coronary artery stent, a US Agency for Healthcare Research and Quality guideline recommends that Acetylsalicylic acid?be taken indefinitely.Frequently, Acetylsalicylic acid?is combined with an ADP receptor inhibitor, such as clopidogrel, prasugrel or ticagrelor to prevent blood clots. This is called dual anti-platelet therapy (DAPT).

Side effects

ContraindicationsAcetylsalicylic acid?should not be taken by people who are allergic to ibuprofen or naproxen , or who have salicylate intolerance[70][71] or a more generalized drug intolerance to NSAIDs, and caution should be exercised in those with asthma or NSAID - precipitated bronchospasm.GastrointestinalAcetylsalicylic acid?use has been shown to increase the risk of gastrointestinal bleeding . Although some enteric-coated formulations of Acetylsalicylic acid?are advertised as being "gentle to the stomach", in one study, enteric coating did not seem to reduce this risk. Combining Acetylsalicylic acid?with other NSAIDs has also been shown to further increase this risk.Central effectsLarge doses of salicylate, a metabolite of Acetylsalicylic acid, have been proposed to cause tinnitus (ringing in the ears) based on experiments in rats, via the action on arachidonic acid and NMDA receptors cascade.Reye syndrome?Reye syndrome, a rare but severe illness characterized by acute encephalopathy and fatty liver, can occur when children or adolescents are given Acetylsalicylic acid?for a fever or other illnesses or infections.

Side effects

The most common adverse effects produced by the Acetylsalicylic acid?are GI disturbances. Occult blood loss from the GI tract, peptic ulceration, and rarely, severe GI hemorrhage can occur. Because salicylic acid is highly bound to plasma proteins, it may be displaced by other highly protein-bound drugs such as oral anticoagulants, sulfonylureas, phenytoin, penicillins, and sulfonamides. The nonacetylated Acetylsalicylic acid?have greatly reduced effects on blood loss and produce fewer adverse GI effects. In addition, they may be somewhat kidney sparing. Acetylsalicylic acid?may provoke hypersensitivity reactions and prolonged bleeding time in some individuals. Tinnitus, hearing impairment, blurred vision, and lightheadedness are indicators of toxic dosages. The use of aspirin in conjunction with any other NSAID is not recommended because of the lack of evidence that such combinations increase efficacy and because of the increased potential for an adverse reaction. Acetylsalicylic acid?are contraindicated in children with febrile viral illnesses because of a possible increased risk of Reye's syndrome

Safety Profile

Poison by ingestion, intraperitoneal, and possibly other routes. Human systemic effects by ingestion: acute pulmonary edema, body temperature increase, changes in kidney tubules, coma, constipation, dehydration, hematuria, hepatitis, nausea or vomiting, respiratory stimulation, somnolence, tinnitus, decreased urine volume. Implicated in aplastic anemia. A 10 gram dose to an adult may be fatal. A human teratogen. Human reproductive effects by ingestion and possibly other routes: menstrual cycle changes, parturition, various effects on newborn including Apgar score, developmental abnormalities of the cardlovascular and respiratory systems. Experimental animal reproductive effects. Human mutation data reported. An allergen; skin contact, inhalation, or ingestion can cause asthma, sneezing, irritation of eyes and nose, hves, and eczema. Combustible when exposed to heat or flame. When heated to decomposition it emits acrid smoke and fumes.

Synthesis

Aspirin, acetylsalicylic acid (3.2.2), is synthesized by the acetylation of salicylic acid (3.2.1) using acetic anhydride or acetyl chloride [60–63].

Potential Exposure

Used as an over-the counter and proprietary pharmaceutical and veterinary drug. Those engagedin manufacture of aspirin or, more likely, in its consumption in widespread use as an analgesic, antipyretic, and antiinflammatory agent

Drug interactions

Potentially hazardous interactions with other drugs ACE inhibitors and angiotensin-II antagonists: antagonism of hypotensive effect, increased risk of nephrotoxicity and hyperkalaemia. Analgesics: avoid concomitant use of 2 or more NSAIDs - increased side effects; avoid with ketorolac - increased risk of side effects and haemorrhage. Antibacterials: possibly increased risk of convulsions with quinolones. Anticoagulants: effects of coumarins enhanced; possibly increased risk of bleeding with edoxaban, heparins and coumarins. Antidepressants: increased risk of bleeding with SSRIs and venlaflaxine. Antidiabetic agents: effects of sulphonylureas enhanced. Antiepileptics: possibly increased phenytoin concentration. Antivirals: increased risk of haematological toxicity with zidovudine; concentration possibly increased by ritonavir. Ciclosporin: may potentiate nephrotoxicity. Cytotoxics: reduced excretion of methotrexate; increased risk of bleeding with erlotinib. Diuretics: increased risk of nephrotoxicity; antagonism of diuretic effect, hyperkalaemia with potassium-sparing diuretics; increased risk of toxicity of acetazolamide with high dose aspirin. Lithium: excretion decreased. Pentoxifylline: increased risk of bleeding. Tacrolimus: increased risk of nephrotoxicity.

Environmental Fate

The toxicity of Acetylsalicylic acid?is multifactorial. Gastrointestinal symptoms such as nausea, vomiting, and abdominal pain occur as a result of both local gastric irritation and stimulation of the medullary chemoreceptor trigger zone. Salicylates directly stimulate the respiratory drive in the brain stem, leading to hyperventilation and respiratory alkalosis. Anion gap metabolic acidosis occurs from a buildup of organic acids as well as the uncoupling of oxidative phosphorylation, which results in an imbalance in ATP consumption and production, resulting in a net buildup of hydrogen ions. Therefore, Acetylsalicylic acid?often causes a mixed acid–base status. Furthermore, the uncoupling of oxidative phosphorylation results in failure to produce ATP despite increased oxygen utilization, which leads to heat production and hyperthermia. Acetylsalicylic acid?interferes with glucose metabolism and gluconeogenesis, and can cause profound decreases in cerebrospinal fluid glucose concentrations despite normal blood glucose concentrations.

Metabolism

After oral doses, absorption of non-ionised Acetylsalicylic acid?occurs in the stomach and intestine. Some Acetylsalicylic acid?is hydrolysed to salicylate in the gut wall. Once absorbed, Acetylsalicylic acid?is rapidly converted to salicylate, but during the first 20 minutes after an oral dose Acetylsalicylic acid?is the main form of the drug in the plasma. Both Acetylsalicylic acid?and salicylate have pharmacological activity although only Acetylsalicylic acid?has an anti-platelet effect. Salicylate is extensively bound to plasma proteins and is rapidly distributed to all body parts.Salicylate is mainly eliminated by hepatic metabolism; the metabolites include salicyluric acid, salicyl phenolic glucuronide, salicylic acyl glucuronide, gentisic acid, and gentisuric acid. The formation of the major metabolites, salicyluric acid and salicyl phenolic glucuronide, is easily saturated and follows Michaelis-Menten kinetics. As a result, steady-state plasma-salicylate concentrations increase disproportionately with dose. Salicylate is also excreted unchanged in the urine; the amount excreted by this route increases with increasing dose and also depends on urinary pH, about 30% of a dose being excreted in alkaline urine compared with 2% of a dose in acidic urine.Renal excretion involves glomerular filtration, active renal tubular secretion, and passive tubular reabsorption.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required

Purification Methods

Crystallise aspirin twice from toluene, wash it with cyclohexane and dry it at 60o under vacuum for several hours [Davis & Hetzer J Res Nat Bur Stand 60 569 1958]. It has been recrystallised from isopropanol and from diethyl ether/pet ether (b 40-60o). It crystallises from EtOH (m 143-144o), *C6H6 (m 143o), hexane (m 115o and 128o), octane (m 121o), and has m 110o after sublimation. It has pK2 6 3.69(H2O), 4.15(20% aqueous EtOH), 4.47(30% aqueous EtOH) and 4.94(40% aqueous EtOH). It is an analgesic. [Beilstein 10 H 67, 10 II 41, 10 III 102, 10 IV 138.]

Toxicity evaluation

As in humans, the environmental fate of acetylsalicylic acid is pH dependent. Above pH 5.5, acetylsalicylic acid will be the predominant form seen. Anions generally do not volatilize or undergo adsorption to the extent of their neutral counterparts. Although information is limited, aspirin is considered readily biodegradable and is ultimately mineralized to carbon dioxide and water.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, carbonates, moisture. Dust dispersed in air is explosive

Waste Disposal

May be flushed to sewer with large volumes of water.

Check Digit Verification of cas no

The CAS Registry Mumber 50-78-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 0 respectively; the second part has 2 digits, 7 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 50-78:
(4*5)+(3*0)+(2*7)+(1*8)=42
42 % 10 = 2
So 50-78-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)/p-1

50-78-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (A2262)  Acetylsalicylic Acid  >98.0%(GC)(T)

  • 50-78-2

  • 25g

  • 98.00CNY

  • Detail
  • TCI America

  • (A2262)  Acetylsalicylic Acid  >98.0%(GC)(T)

  • 50-78-2

  • 500g

  • 295.00CNY

  • Detail
  • Alfa Aesar

  • (A12488)  O-Acetylsalicylic acid, 99%   

  • 50-78-2

  • 100g

  • 99.0CNY

  • Detail
  • Alfa Aesar

  • (A12488)  O-Acetylsalicylic acid, 99%   

  • 50-78-2

  • 500g

  • 275.0CNY

  • Detail
  • Alfa Aesar

  • (A12488)  O-Acetylsalicylic acid, 99%   

  • 50-78-2

  • 2500g

  • 733.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1003)  Aspirin (Acetyl Salicylic Acid)  pharmaceutical secondary standard; traceable to USP, PhEur and BP

  • 50-78-2

  • PHR1003-1G

  • 732.19CNY

  • Detail
  • Sigma-Aldrich

  • (A0200000)  Acetylsalicylicacid  European Pharmacopoeia (EP) Reference Standard

  • 50-78-2

  • A0200000

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001460)  Acetylsalicylic acid for peak identification  European Pharmacopoeia (EP) Reference Standard

  • 50-78-2

  • Y0001460

  • 1,880.19CNY

  • Detail
  • USP

  • (1044006)  Aspirin  United States Pharmacopeia (USP) Reference Standard

  • 50-78-2

  • 1044006-500MG

  • 4,662.45CNY

  • Detail
  • Sigma

  • (A3160)  Acetylsalicylicacid  analytical standard

  • 50-78-2

  • A3160-1VL

  • 1,173.51CNY

  • Detail
  • Sigma

  • (A3160)  Acetylsalicylicacid  analytical standard

  • 50-78-2

  • A3160-5X1VL

  • 4,699.89CNY

  • Detail

50-78-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name acetylsalicylic acid

1.2 Other means of identification

Product number -
Other names 2-Acetoxybenzoic acid,O-Acetylsalicylic acid,ASA

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:50-78-2 SDS

50-78-2Synthetic route

acetic anhydride
108-24-7

acetic anhydride

salicylic acid
69-72-7

salicylic acid

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
In neat (no solvent) Molecular sieve; Microwave irradiation; Green chemistry;100%
With erbium(III) chloride for 0.2h; Heating;99%
With SO42-/ZrO2*graphene oxide solid super acid catalyst at 70℃; for 5h; Reagent/catalyst; Green chemistry;97.1%
methylene-benzo[1,3]dioxin-4-one
302353-24-8

methylene-benzo[1,3]dioxin-4-one

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
With water at 25℃; for 1h; pH=7;100%
acetic acid
64-19-7

acetic acid

salicylic acid
69-72-7

salicylic acid

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
at 80 - 90℃;95%
With sulfuric acid at 70℃; for 5h; Reagent/catalyst;95.7%
2-thioacetoxy-benzoic acid

2-thioacetoxy-benzoic acid

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
With thionyl chloride; dihydrogen peroxide In ethanol at 25℃; for 0.0166667h;95%
With chloro-trimethyl-silane; dihydrogen peroxide In ethanol; water at 25℃; for 0.0666667h; regioselective reaction;88%
With Oxone for 0.583333h;58%
acetyl chloride
75-36-5

acetyl chloride

salicylic acid
69-72-7

salicylic acid

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;86%
With pyridine; sulfuric acid Cooling with ice;59.23%
methoxymethyl 2-acetoxybenzoate

methoxymethyl 2-acetoxybenzoate

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
With bismuth(III) chloride; water In acetonitrile at 50℃; for 1h;85%
2-methylphenyl acetate
533-18-6

2-methylphenyl acetate

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
With zinc(II) oxide In N,N-dimethyl-formamide for 0.15h; microwave irradiation;80%
With potassium permanganate; benzyl(triethyl)ammoniumpermanganate In acetic acid at 30℃; for 72h;24%
With 2,2'-azobis(isobutyronitrile); oxygen; 1N,3N,5N-trihydroxy-1,3,5-triazin-2,4,6[1H,3H,5H]-trione; cobalt(II) acetate; manganese(II) acetate In acetic acid at 150℃; under 760 Torr; for 14h;9%
C16H16N2O5S
85515-88-4

C16H16N2O5S

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
With copper dichloride In tetrahydrofuran; water for 24h; Ambient temperature;80%
acetic anhydride
108-24-7

acetic anhydride

4'-Methoxy-flavyliumchlorid
15402-17-2

4'-Methoxy-flavyliumchlorid

A

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

B

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
With ruthenium(IV) oxide; sodium periodate 1) 5 h, room temp., pyridine; 2) acetic ester, water, 20 min : decomposition reaction;A 79%
B 52%
With ruthenium(IV) oxide; sodium periodate 1) 5 h, room temp., pyridine; 2) water, acetic ester, 20 min; Yield given. Multistep reaction. Yields of byproduct given;
O-acetylsalicylic acid acid 2-oxo-1,2,2-triphenylethyl ester
925681-78-3

O-acetylsalicylic acid acid 2-oxo-1,2,2-triphenylethyl ester

A

13-oxa-indeno[1,2-l]phenanthrene
201-68-3

13-oxa-indeno[1,2-l]phenanthrene

B

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
With air In ethanol; acetonitrile Irradiation;A n/a
B 79%
acetic anhydride
108-24-7

acetic anhydride

salicylaldehyde
90-02-8

salicylaldehyde

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
With oxygen; CoCl2 In 1,2-dichloro-ethane at 25℃; other aldehydes;71.5%
With oxygen; CoCl2 In 1,2-dichloro-ethane at 25℃;71.5%
With oxygen; cobalt(II) chloride In 1,2-dichloro-ethane at 25℃; for 20h;71%
tert-butyl acetylperoxysalicylate
52602-01-4

tert-butyl acetylperoxysalicylate

A

2-acetoxybiphenyl
3271-80-5

2-acetoxybiphenyl

B

Phenyl acetate
122-79-2

Phenyl acetate

C

salicylic acid
69-72-7

salicylic acid

D

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
In benzene at 100℃; for 48h;A 36%
B 10%
C 42%
D 12%
methyl acetylsalicylate
580-02-9

methyl acetylsalicylate

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
With lithium chloride In N,N-dimethyl-formamide for 0.166667h; Microwave irradiation; chemoselective reaction;34%
Stage #1: methyl acetylsalicylate With sodium hydroxide In methanol; water for 2h; Reflux;
Stage #2: With hydrogenchloride
(Z)-1-acetoxy-1-(2-acetoxyphenyl)-1,3-butadiene
129218-88-8

(Z)-1-acetoxy-1-(2-acetoxyphenyl)-1,3-butadiene

A

2-methyl-3-(phenylmethyl)chromone
129218-93-5

2-methyl-3-(phenylmethyl)chromone

B

(E)-1-acetoxy-1-(2-acetoxyphenyl)-1,3-butadiene
129218-92-4

(E)-1-acetoxy-1-(2-acetoxyphenyl)-1,3-butadiene

C

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
In hexane for 2h; Ambient temperature; Irradiation;A 7%
B 30%
C 23%
acetic anhydride
108-24-7

acetic anhydride

salicylic acid
69-72-7

salicylic acid

benzene
71-43-2

benzene

aspirin
50-78-2

aspirin

(2-acetoxy-benzoic acid )-acetic acid-anhydride
18698-59-4

(2-acetoxy-benzoic acid )-acetic acid-anhydride

acetic acid
64-19-7

acetic acid

A

acetic anhydride
108-24-7

acetic anhydride

B

aspirin
50-78-2

aspirin

acetic acid
64-19-7

acetic acid

dibenzoyl peroxide
94-36-0

dibenzoyl peroxide

A

benzoic acid
65-85-0

benzoic acid

B

Phenyl acetate
122-79-2

Phenyl acetate

C

aspirin
50-78-2

aspirin

D

benzene
71-43-2

benzene

sodium salicylate
54-21-7

sodium salicylate

acetyl chloride
75-36-5

acetyl chloride

aspirin
50-78-2

aspirin

Ketene
463-51-4

Ketene

acetone
67-64-1

acetone

salicylic acid
69-72-7

salicylic acid

A

(2-acetoxy-benzoic acid )-acetic acid-anhydride
18698-59-4

(2-acetoxy-benzoic acid )-acetic acid-anhydride

B

aspirin
50-78-2

aspirin

Ketene
463-51-4

Ketene

diethyl ether
60-29-7

diethyl ether

salicylic acid
69-72-7

salicylic acid

aspirin
50-78-2

aspirin

Ketene
463-51-4

Ketene

diethyl ether
60-29-7

diethyl ether

salicylic acid
69-72-7

salicylic acid

A

(2-acetoxy-benzoic acid )-acetic acid-anhydride
18698-59-4

(2-acetoxy-benzoic acid )-acetic acid-anhydride

B

aspirin
50-78-2

aspirin

Ketene
463-51-4

Ketene

salicylic acid
69-72-7

salicylic acid

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
With acetone Behandeln des Reaktionsgemisches mit Wasser;
With acetone Erwaermen des Reaktionsprodukts mit Essigsaeure;
With diethyl ether
With acetone Erwaermen des Reaktionsprodukts mit Essigsaeure;
ethylidene diacetate
542-10-9

ethylidene diacetate

salicylic acid
69-72-7

salicylic acid

aspirin
50-78-2

aspirin

1,1-diacetoxy-2-propene
869-29-4

1,1-diacetoxy-2-propene

salicylic acid
69-72-7

salicylic acid

A

2-vinyl-4H-benzo[d][1,3]dioxin-4-one

2-vinyl-4H-benzo[d][1,3]dioxin-4-one

B

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
With sulfuric acid; acetic acid at 105℃;
dibenzoyl peroxide
94-36-0

dibenzoyl peroxide

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
With acetic acid at 90℃;
2-tert-butoxy-2-methyl-4H-1,3-benzodioxin-4-one
52602-20-7

2-tert-butoxy-2-methyl-4H-1,3-benzodioxin-4-one

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
With phosphate buffer In 1,4-dioxane; water at 37℃; Rate constant;
L-Cysteine
52-90-4

L-Cysteine

aspirin anhydride
1466-82-6

aspirin anhydride

A

S-(O-acetylsalicyloyl)-2-amino-3-thiopropionic acid

S-(O-acetylsalicyloyl)-2-amino-3-thiopropionic acid

B

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
In 1,4-dioxane; water Rate constant; sodium acetate buffer;;
N-acetylcystein
616-91-1

N-acetylcystein

aspirin anhydride
1466-82-6

aspirin anhydride

A

2-acetamido-3-(2-acetoxybenzoylthio)propionic acid

2-acetamido-3-(2-acetoxybenzoylthio)propionic acid

B

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
In 1,4-dioxane; water Rate constant; sodium acetate buffer;;
2-oxopropyl 2-acetoxybenzoate
50785-25-6

2-oxopropyl 2-acetoxybenzoate

A

Salicylsaeure-2-oxopropylester
2100-38-1

Salicylsaeure-2-oxopropylester

B

aspirin
50-78-2

aspirin

Conditions
ConditionsYield
With buffer pH 8.0 In acetonitrile at 37℃; Kinetics; half-life time of hydrolysis at different pH;
aspirin
50-78-2

aspirin

aspirin anhydride
1466-82-6

aspirin anhydride

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃;100%
With iodine; triethylamine; triphenylphosphine In dichloromethane at 0 - 20℃;72%
With triethylamine; trichloroacetonitrile; triphenylphosphine In tetrahydrofuran at 20℃; for 2h;71%
aspirin
50-78-2

aspirin

O-acetylsalicyloyl chloride
5538-51-2

O-acetylsalicyloyl chloride

Conditions
ConditionsYield
Stage #1: aspirin With oxalyl dichloride In dichloromethane at 20℃; for 0.5h;
Stage #2: In dichloromethane; N,N-dimethyl-formamide at 20℃; for 6h;
100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h;98.5%
With 2-hydroxypyridin; thionyl chloride In chloroform at 80 - 85℃;97%
aspirin
50-78-2

aspirin

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

dimethyl 1-(2-acetoxyphenyl)-1-oxomethanephosphonate
62880-92-6

dimethyl 1-(2-acetoxyphenyl)-1-oxomethanephosphonate

Conditions
ConditionsYield
Stage #1: aspirin With oxalyl dichloride In dichloromethane at 20℃;
Stage #2: phosphorous acid trimethyl ester at 5 - 20℃; Further stages.;
100%
aspirin
50-78-2

aspirin

benzyl alcohol
100-51-6

benzyl alcohol

2-acetoxybenzoic acid benzyl ester
52602-17-2

2-acetoxybenzoic acid benzyl ester

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 1h; Reagent/catalyst; Solvent; Temperature; Mitsunobu Displacement; Inert atmosphere;100%
t-butyldimethylsilyl amine
41879-37-2

t-butyldimethylsilyl amine

aspirin
50-78-2

aspirin

tert-butyldimethylsilyl 2-acetoxybenzoate
129512-44-3

tert-butyldimethylsilyl 2-acetoxybenzoate

Conditions
ConditionsYield
In neat (no solvent) at 20℃; for 0.5h; Green chemistry;100%
zyprexa
132539-06-1

zyprexa

aspirin
50-78-2

aspirin

C7H6O3*C17H20N4S
929209-00-7

C7H6O3*C17H20N4S

Conditions
ConditionsYield
In methanol for 24h; Product distribution / selectivity;99%
triethanolamine
102-71-6

triethanolamine

aspirin
50-78-2

aspirin

triethanolamine salicylate
2174-16-5

triethanolamine salicylate

Conditions
ConditionsYield
With methanol for 1h; Reflux;99%
aluminum ethoxide
555-75-9

aluminum ethoxide

aspirin
50-78-2

aspirin

Al(OC2H5)(C6H4OCOCH3COO)2
198878-22-7

Al(OC2H5)(C6H4OCOCH3COO)2

Conditions
ConditionsYield
In xylene acid heated until dissolved (80-85°C), further heating (90-95°C), alcoholate addn., stirring (90-95°C, 3-4 h); drying in vacuum; elem. anal.;98.5%
phenylacetylene
536-74-3

phenylacetylene

aspirin
50-78-2

aspirin

(Z)-β-Styryl acetylsalicylate

(Z)-β-Styryl acetylsalicylate

Conditions
ConditionsYield
Ru(η3-CH2=C(Me)CH2)2 In toluene at 80℃; for 20h;98%
phenylacetylene
536-74-3

phenylacetylene

aspirin
50-78-2

aspirin

1-phenylvinyl 2-acetoxybenzoate

1-phenylvinyl 2-acetoxybenzoate

Conditions
ConditionsYield
With C58H34F18O6P2Ru; silver trifluoromethanesulfonate In toluene at 70℃; for 2h; Inert atmosphere; Schlenk technique; regioselective reaction;98%
aluminum isopropoxide
555-31-7

aluminum isopropoxide

aspirin
50-78-2

aspirin

Al(OC3H7)(C6H4OCOCH3COO)2
198878-23-8

Al(OC3H7)(C6H4OCOCH3COO)2

Conditions
ConditionsYield
In xylene acid heated until dissolved (80-85°C), further heating (90-95°C), alcoholate addn., stirring (90-95°C, 3-4 h); drying in vacuum; elem. anal.;97.8%
vanadocene

vanadocene

aspirin
50-78-2

aspirin

cyclopentadienylvanadium bisacetylsalicylate

cyclopentadienylvanadium bisacetylsalicylate

Conditions
ConditionsYield
In diethyl ether byproducts: C5H6, H2; (vac. or Ar); addn. of acid to V-complex in ether (20°C, 24 h); filtration, washing (ether), drying; elem. anal.;97%
3-hydroxyimino-olean-12-en-28-oic acid
49815-49-8

3-hydroxyimino-olean-12-en-28-oic acid

aspirin
50-78-2

aspirin

17,3-(2-acetoxy)benzoyloxyiminoolean-12-en-28-oic acid

17,3-(2-acetoxy)benzoyloxyiminoolean-12-en-28-oic acid

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In 1,4-dioxane at 20℃;96.9%
With dicyclohexyl-carbodiimide In chloroform at 0 - 20℃; for 2h;62%
With dicyclohexyl-carbodiimide In 1,4-dioxane at 20℃;
aluminum isopropoxide
555-31-7

aluminum isopropoxide

aspirin
50-78-2

aspirin

Al(C6H4OCOCH3COO)3
29825-08-9

Al(C6H4OCOCH3COO)3

Conditions
ConditionsYield
In xylene acid heated until dissolved (80-85°C), further heating (90-95°C), alcoholate addn., stirring (90-95°C, 3-4 h); drying in vacuum; elem. anal.;96.5%
aluminum isopropoxide
555-31-7

aluminum isopropoxide

aspirin
50-78-2

aspirin

Al(OC3H7)2C6H4OCOCH3COO
198878-21-6

Al(OC3H7)2C6H4OCOCH3COO

Conditions
ConditionsYield
In xylene acid heated until dissolved (80-85°C), further heating (90-95°C), alcoholate addn., stirring (90-95°C, 3-4 h); drying in vacuum; elem. anal.;96%
2,2'-iminobis[ethanol]
111-42-2

2,2'-iminobis[ethanol]

aspirin
50-78-2

aspirin

bis(2-hydroxy-ethyl)ammonium 2-hydroxy-benzoate
109962-24-5

bis(2-hydroxy-ethyl)ammonium 2-hydroxy-benzoate

Conditions
ConditionsYield
With methanol for 1h; Reflux;96%
2-(Diethylamino)ethanol
100-37-8

2-(Diethylamino)ethanol

aspirin
50-78-2

aspirin

diethylaminoethylacetylsalicylate acetylsalicylate

diethylaminoethylacetylsalicylate acetylsalicylate

Conditions
ConditionsYield
Stage #1: aspirin With dicyclohexyl-carbodiimide In chloroform at 5 - 20℃; for 2h;
Stage #2: 2-(Diethylamino)ethanol at 20℃; for 3h;
96%
2-(Diethylamino)ethanol
100-37-8

2-(Diethylamino)ethanol

aspirin
50-78-2

aspirin

diethylaminoethyl acetylsalicylate acetylsalicylic acid salt

diethylaminoethyl acetylsalicylate acetylsalicylic acid salt

Conditions
ConditionsYield
Stage #1: aspirin With dicyclohexyl-carbodiimide In chloroform at 5 - 20℃; for 2h;
Stage #2: 2-(Diethylamino)ethanol In chloroform at 20℃; for 3h;
96%
Stage #1: aspirin With dicyclohexyl-carbodiimide In chloroform at 5 - 20℃; for 2h;
Stage #2: 2-(Diethylamino)ethanol In chloroform at 20℃; for 3h;
96%
ethambutol
74-55-5

ethambutol

aspirin
50-78-2

aspirin

C19H30N2O5

C19H30N2O5

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dimethyl sulfoxide at 30℃; Temperature;96%
fluoroiodomethane
373-53-5

fluoroiodomethane

aspirin
50-78-2

aspirin

fluoromethyl 2-acetoxybenzoate

fluoromethyl 2-acetoxybenzoate

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 20℃; for 6h; chemoselective reaction;96%
exo-7-chloro-endo-7-phenyl-cis-bicyclo<4.2.0>octan-8-one
103150-19-2

exo-7-chloro-endo-7-phenyl-cis-bicyclo<4.2.0>octan-8-one

aspirin
50-78-2

aspirin

exo-1-<(2-acetoxybenzoyl)oxy>-7-phenyl-cis-bicyclo<4.2.0>octane-8-one
122898-94-6

exo-1-<(2-acetoxybenzoyl)oxy>-7-phenyl-cis-bicyclo<4.2.0>octane-8-one

Conditions
ConditionsYield
With triethylamine In acetone at 20℃;95%
aspirin
50-78-2

aspirin

salicylic acid
69-72-7

salicylic acid

Conditions
ConditionsYield
With water; trifluoroacetic acid at 65℃; for 0.5h;95%
With copper dichloride In methanol; water for 1h; Heating;90%
With sodium hydroxide In 1,4-dioxane at 56.4℃; Rate constant; pH 12; reaction in the presence of aq. cetyltrimethylammonium bromide (CTBA);
2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

aspirin
50-78-2

aspirin

2-acetoxy-benzoic acid pentafluorophenyl ester
65482-79-3

2-acetoxy-benzoic acid pentafluorophenyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 40℃; for 0.333333h; microwave irradiation;95%
With dicyclohexyl-carbodiimide In 1,4-dioxane for 4h;61%
propargyl bromide
106-96-7

propargyl bromide

aspirin
50-78-2

aspirin

Acetylsalicylic acid propargylic ester

Acetylsalicylic acid propargylic ester

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2h;95%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
Stage #1: aspirin With potassium carbonate In N,N-dimethyl-formamide for 0.5h;
Stage #2: propargyl bromide In N,N-dimethyl-formamide at 60℃; for 10h;
aspirin
50-78-2

aspirin

lysine Acetylsalicylate
62952-06-1

lysine Acetylsalicylate

Conditions
ConditionsYield
In ethanol; water for 0.533333h; Time;95%
In water; acetone at -15 - 15℃; for 1h; Concentration;92.4%
3-hydroxyimino-olean-12-en-28-oic acid methyl ester
35137-30-5

3-hydroxyimino-olean-12-en-28-oic acid methyl ester

aspirin
50-78-2

aspirin

13,3-(2-acetoxy)benzoyloxyiminoolean-12-en-28-oic acid methyl ester

13,3-(2-acetoxy)benzoyloxyiminoolean-12-en-28-oic acid methyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In 1,4-dioxane at 20℃;93.9%
With dicyclohexyl-carbodiimide In chloroform at 0 - 20℃; for 2h;67%
With dicyclohexyl-carbodiimide In 1,4-dioxane at 20℃;

50-78-2Relevant articles and documents

-

Drevina et al.

, (1976)

-

Two Keggin polyoxometalate-based hybrid compounds with different helix: Syntheses, structure and catalytic activities

Zhu, Peipei,Sheng, Ning,Liu, Guodong,Sha, Jingquan,Yang, Xiya

, p. 52 - 58 (2017)

By adjusting pH value, two new Keggin polyoxometalate-based hybrid compounds with different helical structure, [Ag6(btp)(pyttz)6·(HSiMo12O40)2]·4H2O (1) and [Ag2(pyttz)4·(H2SiMo12O40)2]·(TMA)2·4H2O (2), (pyttz?=?3-(pyrid-4-yl)-5-(1?H-1,2,4–3-yl)-1,2,4-triazolyl, btp?=?5,5′-di(pyridin-4-yl)-1?H,1′H-3,3′-bi(1,2,4-triazole), TMA?=?tetramethylammonium), were successfully isolated by hydrothermal reaction and structurally characterized. Structural analysis shows the nature of the inorganic meso-helical channel in compound 1 and 2D homological helical layer in compound 2. It is also interesting that a new organic ligand btp is formed in situ by the coupling of N-Heterocycle in 1. In addition, the catalytic activities of 1 and 2 as solid-acid catalyst are explored, and the results indicate that 1 and 2 are a kind of highly-efficient and promising solid catalysts. Additionally, the proposed generation mechanism of btp in situ is also discussed.

Raman spectrum online monitoring in aspirin synthesis process

Su, Hui,Sun, Kuo,Yao, Zhixiang,Huang, Peixian,Liu, Liu

, p. 467 - 471 (2014)

In this work, the Raman spectra were obtained directly in the synthesis process of aspirin as prediction set. The concentration sample according to the amount of material changes before and after reaction and it's extracted Raman information made up training set and a quantitative analysis model of the salicylic acid-acetic anhydride-aspirin mixed system was established by applying partial least squares (PLS). The values of correlation coefficient squared between measured and regression (R2), root mean square error of prediction set (RMSEP), mean deviation (MD) indicate that the influence of the prediction precision by the baseline drift can be effectively reduced in the method of spectrum pretreatment via mormalize + savitzky-go1ay smoothing first derivative. After the prediction set was used in this analysis mode, the mass per cent between salicylic acid and aspirin of online monitoring was 4.59 %, while the off-line Raman analysis and high performance liquid chromatography analysis results were 5.66 and 2.75 %. The relative deviations were -1.07 and 1.84 %. This method provides effective data support for synthesis of aspirin Raman spectroscopy online monitoring.

Evaluation and establishment of a cleaning protocol for the production of vanisal sodium and aspirin using a continuous oscillatory baffled reactor

Ricardo, Caldeira,Xiongwei, Ni

, p. 1080 - 1087 (2009)

The robustness and adaptability of a continuous oscillatory baffled reactor (COBR) in organic syntheses of vanisal sodium and aspirin were tested whilst meeting the stringent regulatory standards. In one week-long continuous operation, vanisal sodium was produced to a purity level of 99.94%, aspirin to a level of 99.57%. The loss of product during the cleaning process amounted to 0.001% and 0.005% for vanisal sodium and aspirin, respectively. The data of the continuous syntheses show that the operation of the COBR is robust and consistent throughout the week-long period. The cleaning stage that was used after each production campaign exhibited a first-order kinetics and was effective and efficient.

On the polymorphism of aspirin: Crystalline aspirin as intergrowths of two "polymorphic" domains

Bond, Andrew D.,Boese, Roland,Desiraju, Gautam R.

, p. 618 - 622 (2007)

Aspirin: No end to the headaches? The two known crystalline arrangements of aspirin are so closely related that aspirin crystals form intergrowth structures containing domains of form I and domains of form II. The ratio and distribution of the domains is variable among aspirin samples, raising questions for the definition of the term polymorph in this case. (Figure Presented).

S-Acylation of cysteine by O-acetylsalicylic anhydride: A possible mechanism for aspirin hypersensitivity?

Dannan,Khawam,Bogardus,Hussain,Crooks

, p. 1081 - 1084 (1986)

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BiCl3-Facilitated removal of methoxymethyl-ether/ester derivatives and DFT study of -O-C-O- bond cleavage

Pacherille, Angela,Tuga, Beza,Hallooman, Dhanashree,Dos Reis, Isaac,Vermette, Mélodie,Issack, Bilkiss B.,Rhyman, Lydia,Ramasami, Ponnadurai,Sunasee, Rajesh

supporting information, p. 7109 - 7116 (2021/05/03)

A simple method for the cleavage of methoxymethyl (MOM)-ether and ester derivatives using bismuth trichloride (BiCl3) is described. The alkyl, alkenyl, alkynyl, benzyl and anthracene MOM ether derivatives, as well as MOM esters of both aliphatic and aromatic carboxylic acids, were deprotected in good yields. To better understand the molecular roles of BiCl3and water for MOM cleavage, two possible binding pathways were investigated using the density functional theory (DFT) method. The theoretical results indicate the differential initial binding site preferences of phenolic and alcoholic MOM substrates to the Bi atom and suggest that water plays a key role in facilitating the cleavage of the MOM group.

Synthesizing method of acetylsalicylic acid

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Paragraph 0059; 0064; 0065, (2019/03/08)

The invention relates to a synthesizing method of acetylsalicylic acid. The synthesizing method comprises the following steps: a rare-earth modified solid superacid catalyst is provided, the solid superacid catalyst comprises a composite carrier, sulfate radicals bonded to the composite carrier, and rare earth ions doped with the composite carrier, wherein the composite carrier is formed by silicon dioxide and aluminum oxide which are composited; and salicylic acid and acetic anhydride react under the effect of the rare-earth modified solid superacid catalyst, and then the acetylsalicylic acidis obtained. According to the synthesizing method of the acetylsalicylic acid, rare-earth modified solid superacid serves as the catalyst, the salicylic acid and the acetic anhydride serve as the rawmaterials of an acetylation reaction to prepare the acetylsalicylic acid, in the process of the acetylation reaction, the product yield is high, corrosion of the catalyst to equipment is small, pollution to the environment is small, the recyclable rate of the catalyst is high, the product aftertreatment process is simplified, and energy consumption is low.

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