63-74-1 Usage
Chemical Description
Sulfanilamide is then treated with isothiocyanates to produce 1-aroyl/alkanoyl-3-(4-aminosulfonyl phenyl)thioureas.
Description
Sulfanilamide is an organic sulfur compound structurally similar to p-aminobenzoic acid (PABA) with antibacterial property. Sulfanilamide competes with PABA for the bacterial enzyme dihydropteroate synthase, thereby preventing the incorporation of PABA into dihydrofolic acid, the immediate precursor of folic acid. This leads to an inhibition of bacterial folic acid synthesis and de novo synthesis of purines and pyrimidines, ultimately resulting in cell growth arrest and cell death.
Uses
Used in Pharmaceutical Industry:
Sulfanilamide is used as the main raw material for the synthesis of sulfa drugs, which are a class of antimicrobial agents effective against a wide range of bacterial infections.
Used in Chemical Analysis:
Sulfanilamide is used as a reagent to determine nitrite, a common analyte in various chemical and environmental tests.
Used in Synthesis of Other Compounds:
Sulfanilamide serves as an intermediate for the preparation of 2,6-disubstituted anilines by electrophilic substitution, followed by removal of the sulfonamide blocking group by desulfonation with sulfuric acid.
Used in Veterinary Medicine:
Sulfanilamide is used as a topical anti-inflammatory drug in veterinary medicine, helping to manage inflammation and infection in animals.
Used in Wound Disinfection:
Sulfanilamide is used as an intermediate for the synthesis of other sulfa drugs and even for wound disinfection, providing antibacterial effects on various Gram-positive and negative bacteria.
Used in Herbicide Production:
Amino benzene sulfonamide, derived from sulfanilamide, is an intermediate of herbicide asulam, contributing to the development of agricultural chemicals for weed control.
Used in Antimicrobial Applications:
Sulfanilamide is an antibacterial and antimicrobial agent of the sulfonamide type, used topically and vaginally to treat infections such as vaginal yeast infections. It acts as a competitive inhibitor of dihydropteroate synthase to block the synthesis of folic acid, essential for bacterial growth.
Product features
Sulfanilamide is an organic sulfur compound structurally similar to p-aminobenzoic acid (PABA) with antibacterial property. Sulfanilamide competes with PABA for the bacterial enzyme dihydropteroate synthase, thereby preventing the incorporation of PABA into dihydrofolic acid, the immediate precursor of folic acid. This leads to an inhibition of bacterial folic acid synthesis and de novo synthesis of purines and pyrimidines, ultimately resulting in cell growth arrest and cell death.Without it, bacteria cannot replicate.
Mechanism of action: mechanism of action is to interfere with the synthesis of nucleic acids required for pathogenic microorganisms,making bacteria lack of nutrition and stop the growth, development and reproduction, having suppression killing effect on hemolytic streptococcus, staphylococcus and meningococcal.
Pharmacodynamics: Oral easily absorbed from the gastrointestinal tract, widely distributed in the body, can penetrate the blood-brain barrier into the brain tissue, and can penetrate the placental barrier into the fetus. Rapid excretion, mainly excreted in metabolites from kidney.
Clinical application: Mainly used for trauma infection caused by infection hemolytic streptococcus, staphylococcus, and local wound infections.
Uses: Sulfanilamide is lower toxicity in sulfa drugs, can be applied for infants, pregnant women, pregnant women and during menstruation, but not in large doses. Having effects on hemolytic streptococcal infection (erysipelas, puerperal fever, tonsillitis), urinary tract infection (gonorrhea) and so; also the intermediate for synthesis of other sulfa drug (such as sulfa amidine, pyrimidine and sulfamethoxazole sulfa methoxy-triazine, etc. ).
Production methods
There are several methods for their preparation.
1. Acetyl aniline used as raw material
The acetanilide reacts with chlorosulfonic acid at 40~50 ℃, and then cooled slowly, added to water for acid decomposition, while precipitation, dried and filtered to give acetaminophen chloride and ammoniated, ammoniated temperature is controlled at 40~45 ℃, hydrolysis, acidification.
2. Method of mixed diphenyl urea
Condensation of aniline and urea is single-phenylurea and diphenyl urea (called mixed urea), and then obtained from chlorosulfonated, amination, hydrolysis, acid precipitation. The reaction procedure is as follows.
(1)Condensation condensation of aniline hydrochloride and urea, at a temperature of 101~110 ℃ reaction for 3~4 h, obtaining mixed diphenyl urea.
(2)Chlorosulfonated Chlorine acid is pressed into the sulfonated pot, stirring cooling, when the temperature drops below 10 ℃, uniformly added mixed phenyl urea under stirring, the reaction temperature is gradually increased, the addition is completed, at the 46~50 ℃ insulation and mixing for 2 h, cooled to below 10 ℃, added water for acid decomposition. Controlling that the decomposition temperature does not exceed 15 ℃, after the addition of water continued stirring for 20min, then by precipitation, washed with water, obtaining mixed phenylurea chloride.
(3)Ammoniated 2% aqueous ammonia is put into ammoniated pan, cooled to 25 ℃, stirring and added into a mixing phenyl urea chloride, control the temperature at 40 ℃, insulation and reaction for 3h, obtaining ammoniated liquid.
(4)Hydrolysis and neutralization The amide is heated up to 90 ℃, is added 3% lye, continue to heat 108~112 ℃, hydrolysis for 5 h, and moved in the crystallization pot, added hydrochloric acid to neutralize crystals and the crystals are cooled to 20 ℃, crystallization, filtration, washed with water, dry, products are obtained.
Preparation
Sulfonamide is synthesized from acetanilide by chlorosulfonation, amination, hydrolysis, and neutralization:Acetanilide is reacted with chlorosulfonic acid at 40~50℃, then cooled, slowly added to water for acid decomposition, precipitated at the same time, dried and filtered to obtain p-acetamidobenzenesulfonyl chloride, and then subjected to ammoniation, and the amination temperature is controlled at 40~ 45 ℃, and then hydrolyzed, acidified to obtain sulfonamide.
World Health Organization (WHO)
Sulfanilamide, a sulfonamide anti-infective agent, was introduced
in 1936 for the treatment of bacterial infections. The importance of sulfonamides
has subsequently decreased as a result of increasing resistance and their
replacement by antibiotics which are generally more active and less toxic. The
sulfonamides are known to cause serious adverse effects such as renal toxicity,
sometimes fatal exfoliative dermatitis and erythema multiforma and dangerous
adverse reactions affecting blood formation such as agranulocytosis and
haemolytic or aplastic anaemia. Sulfanilamide is still used in some countries as a
pessaries or as vaginal cream.
Synthesis Reference(s)
Chemical and Pharmaceutical Bulletin, 9, p. 71, 1961 DOI: 10.1248/cpb.9.71
Antimicrobial activity
Sulfanilamide is a sulfonamide antibiotic. It is bacteriostatic against Streptococci in vitro at a concentration of 20 μg/ml and inhibits the growth of 106 clinically isolated strains of Gonococcus. Sulfanilamide reduces the concentration of Streptococcus in rabbit plasma ex vivo following four doses of 20 ml of a 2% sulfanilamide solution. Sulfonamide class antibiotics, of which sulfanilamide is a member, are bacteriostatic and inhibit bacterial synthesis of dihydrofolic acid by competing with 4-aminobenzoic acid for binding to dihydropteroate synthase. Formulations containing sulfanilamide have been used to treat T. vaginalis infections.
Air & Water Reactions
May be unstable if exposed for long periods air and light . Slightly water soluble.
Reactivity Profile
Sulfanilamide is an amino acid. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May react with azo and diazo compounds to generate toxic gases.
Fire Hazard
Flash point data for Sulfanilamide are not available but Sulfanilamide is probably combustible.
Biochem/physiol Actions
Sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase.Mode of Action: A competitive inhibitor of dihydropteroate synthestase to block the synthesis of folic acid.Anti-microbial Spectrum: Gram positive, Gram negative, Chlamydia Mode of Resistance: Alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.
Safety Profile
Poison by intraperitoneal route. Moderately toxic by ingestion, subcutaneous, and intravenous routes. Human teratogenic effects by unspecified route: developmental abnormalities of the blood and lymphatic systems (including the spleen and bone marrow). Experimental reproductive effects. Questionable carcinogen with experimental carcinogenic data. Mutation data reported. Implicated in aplastic anemia. When heated to decomposition it emits very toxic fumes of NOx and SOx.
Check Digit Verification of cas no
The CAS Registry Mumber 63-74-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 3 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 63-74:
(4*6)+(3*3)+(2*7)+(1*4)=51
51 % 10 = 1
So 63-74-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)
63-74-1Relevant articles and documents
Electrochemical Behavior of Azobenzene-4,4'-disulfonamide at Pyrolitic Graphite Electrode
Goyal, R. N.,Srivastava, Amit Kumar
, p. 205 - 211 (1993)
The electrochemical reduction of azobenzene-4,4'-disulfonamide (1), an oxidation product of sulfanilamide, has been studied at Pyrolytic graphite electrode, over a wide pH range of 3.0 to 10.6 in the Britton Robinson buffers, by electrochemical and spectroscopic techniques.Under cyclic voltammetric conditions the 2e-, 2H+ reduction of this compound was found to give hydrazobenzene-4,4'-disulfonamide which has been characterised using IR, mp, mass and NMR spectra.Under controlled potential electrolysis, the presence of two electron withdrawing -SO2NH2 groups was found to cause the slow disproportionation -3 s-1> of the hydrazo compound and sulfanilamide has been found as the major product of reduction.A plausible mechanism for the ECE reduction of 1 is suggested.
Synthesis of new Copper Catalyst with Pyrazole Based Tridentate Ligand and Study of Its Activity for Azide Alkyne Coupling
Rajeswari, Panneer Selvam,Nagarajan, Rajendran,P, Sujith K,Emmanuvel, Lourdusamy
supporting information, (2020/12/03)
Synthesis of new copper catalyst with pyrazole based tridentate ligand and study of its activity for azide alkyne coupling were investigated by researchers. To a solution of acetyl acetone (2.002 g, 20 mmol), 2- nitrophenylhydrazine in ethanol was added five drops of con. HCl and heated at 50° for 1 hour. After confirming the formation of 3, 5-dimethyl-1-(2-nitrophenyl)- 1H-pyrazole by TLC, ice cooled water was added in to the reaction mixture. The precipitate was filtered, washed with water and then hexane. The product formed as yellow precipitate, that precipitate had been filtered by normal filter paper. The product was recrystallized in ethanol. For synthesis, was suspended in 6 mL of deionized and stirred for 4 h until a clear solution was obtained in 50 ml round bottom flask Cu(OAc) 2. The reaction mixture was diluted with water, filtered, washed sequentially with water, methanol and n-hexane. Then dark greenish blue color crystal were formed and used for the reactions. The solid was crystallized in CH2Cl2 to get crystal whose structure was confirmed by single crystal XRD.
Yeast supported gold nanoparticles: an efficient catalyst for the synthesis of commercially important aryl amines
Krishnan, Saravanan,Patel, Paresh N.,Balasubramanian, Kalpattu K.,Chadha, Anju
supporting information, p. 1915 - 1923 (2021/02/06)
Candida parapsilosisATCC 7330 supported gold nanoparticles (CpGNP), prepared by a simple and green method can selectively reduce nitroarenes and substituted nitroarenes with different functional groups like halides (-F, -Cl, -Br), olefins, esters and nitriles using sodium borohydride. The product aryl amines which are useful for the preparation of pharmaceuticals, polymers and agrochemicals were obtained in good yields (up to >95%) using CpGNP catalyst under mild conditions. The catalyst showed high recyclability (≥10 cycles) and is a robust free flowing powder, stored and used after eight months without any loss in catalytic activity.