3998-25-2

Basic information

• Product Name: Acetyl isocyanate
• Synonyms: Acetyl isocyanate
• CAS NO: 3998-25-2
• Molecular Formula: C₃H₃NO₂
• Molecular Weight: 85.06142
• Mol File: 3998-25-2.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 79-80 °C
• Appearance: /
• Density: 1.0826 g/cm3(Temp: 25 °C)
• CAS DataBase Reference: Acetyl isocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: Acetyl isocyanate(3998-25-2)
• EPA Substance Registry System: Acetyl isocyanate(3998-25-2)

Safety Data

• Hazardous Substances Data: 3998-25-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Acetyl isocyanate is used as a raw material for the synthesis of various pharmaceutical compounds. Its high reactivity allows for the creation of a wide range of medicinal agents, contributing to the development of new treatments and therapies.
Used in Pesticide Production:
In the agricultural sector, acetyl isocyanate serves as a key component in the manufacturing of pesticides. Its reactive nature enables the production of effective pest control agents, helping to protect crops and ensure food security.
Used in Polymer and Polyurethane Foam Manufacturing:
Acetyl isocyanate is utilized in the production of polyurethane foams and other polymers. Its incorporation into these materials enhances their properties, such as durability and flexibility, making them suitable for various applications in industries like construction, automotive, and furniture.
Due to the high toxicity and corrosiveness of acetyl isocyanate, it is crucial to handle this chemical with extreme caution and follow all safety guidelines to prevent accidents and ensure the well-being of individuals involved in its production and use.

Upstream product

• 1118-02-1 trimethylsilyl isocyanate 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 51060-05-0 fulminic acid 
• 60-35-5 acetamide 
• 79-37-8 oxalyl dichloride 
• 994-30-9 triethylsilyl chloride 
• 39042-51-8 (C₃H₇)3SnOC(CH₃)NCOOCH₃ 
• 10416-58-7 N,N-bis(trimethylsilyl)acetamide 
• 92114-96-0 mercury fulminate 
• 75-44-5 phosgene 
• 681-99-2 tributyltin isocyanate 
• 917-61-3 sodium isocyanate 
• 3315-16-0 silver cyanate 

Downstream Products

• 638-20-0 N,N'-diacetylurea 
• 2597-54-8 ethyl acetylcarbamate 
• 860752-29-0 acetylcarbamoyloxy-phenyl-acetic acid 
• 60-35-5 acetamide 
• 591-07-1 acetylurea 
• 36232-17-4 9,10-Bis-acetylcarbamoyloxy-anthracen 
• 136179-59-4 2-methyl-4-acetoxy-6H-1,3-oxazin-6-one 
• 133902-78-0 4-acetyl-1-(2,4-dichlorophenyl)-3,3-dimethyl-1,2,4-triazolidin-5-one 
• 133902-74-6 4-acetyl-1-(4-chlorophenyl)-3,3-dimethyl-1,2,4-triazolidin-5-one 
• 133902-76-8 4-acetyl-1-(4-methoxyphenyl)-3,3-dimethyl-1,2,4-triazolidin-5-one 
• 133902-70-2 4-acetyl-1-phenyl-3,3-dimethyl-1,2,4-triazolidin-5-one 
• 93823-22-4 methyl 3-acetylamino-2-methyl-3-oxopropanoate 
• 133902-77-9 4-acetyl-1-(2-chlorophenyl)-3,3-dimethyl-1,2,4-triazolidin-5-one 
• 133902-75-7 4-acetyl-1-(4-fluorophenyl)-3,3-dimethyl-1,2,4-triazolidin-5-one 

Relevant articles and documents

Design, Synthesis, and Insecticidal Activity of Novel Doramectin Derivatives Containing Acylurea and Acylthiourea Based on Hydrogen Bonding

Our recent investigation on the insecticidal activities of several doramectin derivatives preliminarily revealed that the presence of hydrogen bonds at the C4″ position of the molecule with target protein γ-aminobutyric acid (GABA) receptor was crucial for retaining high insecticidal activity. As a continuation of our research work on the development of new insecticides, two series of novel acylurea and acylthiourea doramectin derivatives were designed and synthesized. The bioassay results indicated that the newly synthesized compounds (5o, 5t, and 6t) exhibited higher insecticidal activity against diamondback moth, oriental armyworm, and corn borer than the control compounds doramectin, commercial avermectins, chlorbenzuron, and lead compound 3g in our laboratory. Specifically, compound 5t was identified as the most promising insecticide against diamondback moth, with a final mortality rate of 80.00% at the low concentration of 12.50 mg/L, showing approximately 7.75-fold higher potency than the parent doramectin (LC50 value of 48.1547 mg/L), 6.52-fold higher potency than commercial avermectins (LC50 value of 40.5507 mg/L), and 3.98-fold higher potency than compound 3g (LC50 value of 24.7742 mg/L). Additionally, molecular docking simulations revealed that compound 5t (2.17, 2.20, 2.56, and 2.83 ?) displayed stronger hydrogen-bond action in binding with the GABA receptor, better than that of compound 5o (1.64 and 2.15 ?) and compound 6t (2.20 and 2.31 ?) at the C4″ position. This work demonstrated that these compounds containing hydrogen-bond groups might contribute to the improvement of insecticidal activity and supply certain hints toward structure optimization design for the development of new insecticides.

Mutual prodrugs containing bio-cleavable and drug releasable disulfide linkers

We report herein the design and synthesis of several representative examples of novel mutual prodrugs containing nine distinct types of self-immolative drug-releasable disulfide linkers with urethane, ester, carbonate, or imide linkages between the linker and any two amine/amide/urea (primary or secondary) or carboxyl or hydroxyl (including phenolic)-containing drugs. We also report drug release profiles of a few representative mutual prodrugs in biological fluids such as simulated gastric fluid and human plasma. We also propose plausible mechanisms of drug release from these mutual prodrugs. We have also conducted a few mechanistic studies based on suggested sulfhydryl-assisted cleavage of mutual prodrugs and characterized a few important metabolites to give support to the proposed mechanism of drug release from the reported mutual prodrugs.

One-pot addition-intramolecular N-cyclization of carbamates mediated by alkali metallic reagents as an approach to 4-(fluoroalkyl)oxazolidin-2-ones

A mild and straightforward strategy for the synthesis of 4-(fluoroalkyl)oxazolidin-2-ones via one-pot addition-intramolecular N-cyclization of allyl carbamates with fluoroalkyl iodides is presented. The reaction proceeded in moderate to good yield through regiocontrol and an increase in the reactivity of the ambident nucleophiles by the use of alkali metallic reagents. Georg Thieme Verlag Stuttgart. New York.

Preparation and physicochemical characterization of a novel water-soluble prodrug of carbamazepine

N-Acyl-urea derivatives of carbamazepine (CBZ) were synthesized through the reactions of iminostilbene with acyl-isocyanates to form N-glycyl-carbamazepine (N-Gly-CBZ, after a deprotection step) or N-acetyl-carbamazepine (N-acetyl-CBZ). N-Gly-CBZ was isolated as its water-soluble HCl salt and was designed to act as a prodrug and convert to CBZ and glycine in vivo by enzymatic cleavage of the acyl-urea bond. The stability pH-rate profiles for N-Gly-CBZ and N-acetyl-CBZ were determined. The stability of N-Gly-CBZ was found to range over four orders of magnitude with its greatest stability at pH 3-4 and a t 90 value of 5.9 day at pH 4 at 25°C. From the fit of the pH rate profile two pKa values were estimated to be 7.2 (terminal amine) and 10.0 (imide), which were independently verified using UV-visible spectroscopic analysis. The solubility of N-Gly-CBZ in aqueous solution was determined in the range of pH 5.5-7.5. The intrinsic solubility of the neutral form of the prodrug was found to be 4.4 mg/mL, and the solubility of the prodrug increased exponentially (log linear) as pH was decreased below its pKa1 value. N-Gly-CBZ was found to have an aqueous solubility in excess of 50 mg/mL at pH 4. The presence of N-Gly-CBZ was found to increase the aqueous solubility of CBZ, a degradation product. CBZ showed an 8.6-fold greater solubility in an aqueous solution containing 23 mg/mL of N-Gly-CBZ than in water alone. The solubilization of CBZ by N-Gly-CBZ was investigated by examining the diffusion coefficients of the predominant species in D2O and was found to be more consistent with stacking complex formation than micelle formation. The stability ofN-Gly-CBZ makes a ready-to-use parenteral formulation impractical, but a freeze-dried preparation for reconstitution appears to be feasible.

MORPHINAN DERIVATIVES OF ORGANIC AND INORGANIC ACIDS

Novel 4,5-epoxy-14-substituted morphinan derivatives of organic and inorganic acids are disclosed. Pharmaceutical compositions containing the compounds and methods of their pharmaceutical uses and syntheses are also disclosed. The compounds disclosed are useful, inter alia, as modulators of opioid receptors.

Synthesis and activity evaluation of phenylurea derivatives as potent antitumor agents

We have discovered several tubulin-active compounds in our previous studies. In the establishment of a compound library of small molecule weight tubulin ligands, 14 new N-3-haloacylaminophenyl-N′-(alkyl/aryl) urea analogs were designed and synthesized. The structure-activity relationship (SAR) analysis revealed that (i) the order of anticancer potency for the 3-haloacylamino chain was following -CH2Br > -CHBrCH3; (ii) the N′-substituent moiety was not essential for the anticancer activity, and a proper alkyl substitution might enhance the anticancer activity. Among these analogs, the compounds 16j bearing bromoacetyl at the N′-end exhibited a potent activity against eight human tumor cell lines, including CEM (leukemia), Daudi (lymphoma), MCF-7 (breast cancer), Bel-7402 (hepatoma), DU-145 (prostate cancer), DND-1A (melanoma), LOVO (colon cancer) and MIA Paca (pancreatic cancer), with the IC50 values between 0.38 and 4.07 μM. Interestingly, compound 16j killed cancer cells with a mechanism independent of the tubulin-based mechanism, indicating a significant change of the action mode after the structure modification.

Carbamoyloxy derivatives of mutiline and their use as antibacterials

PCT No. PCT/EP96/05874 Sec. 371 Date Dec. 4, 1998 Sec. 102(e) Date Dec. 4, 1998 PCT Filed Dec. 19, 1996 PCT Pub. No. WO97/25309 PCT Pub. Date Jul. 17, 1997Derivatives of mutiline of formula (1A) and pharmaceutically acceptable salts and derivatives thereof, in which R1 is ethyl or vinyl, Y is a carbamoyloxy group, in which the N-atom is unsubstituted, or mono- or di-substituted, are useful in the treatment of bacterial infections.

Method of preparing acylisocyanates

The invention relates to a novel process for the preparation of acyl isocyanates which consists in reacting oxalyl chloride with an N-trialkylsilylcarboxamide or an N,N-bis(trialkylsilyl)carboxamide. The process makes it possible to obtain acyl isocyanates in good yield, in particular acyl isocyanates derived from aliphatic amides, and under simplified reaction conditions.

Synthesis and cycloadditions of 1-alkenyl isocyanates

1-alkenyl isocyanates 1a and 1b have been conveniently prepared from acetyl or propionyl chloride, silver cyanate and tert-butyldimethylsilyl triflate in the presence of triethylamine.They react with electron-deficient acetylenic dienophiles or with tosyl cyanide to give highly functionalised pyridines or derivatives of uracil or thymine in moderate yields.They also cycloadd with 1-(diethylamino)prop-1-yne, an electron-rich dienophile, to yield glutaconimides and pyridine derivatives. - Keywords; alkenyl isocyanate; Diels-Alder reaction; pyridine; uracil; thymine; glutaconimide

Acyl carbamate directing groups in nucleoside synthesis: Applications in the synthesis of 2′-deoxy-5-ethyl-4′-thiouridine

The use of the 3-O-(N-acyl)carbamoyl directing groups in the synthesis of the potent anti-Herpes virus agent 2′-deoxy-5-ethyl-4′-thio-D-uridine is described. This includes details of experiments to optimise the carbamate substitution and a multi-gram exemplification of the key steps.