3555-94-0

Basic information

• Product Name: VINYL ISOCYANATE 97
• Synonyms: CH2=CHNCO;VINYL ISOCYANATE 97;Ethenyl isocyanate
• CAS NO: 3555-94-0
• Molecular Formula: C₃H₃NO
• Molecular Weight: 69.0627
• EINECS: 222-616-0
• Product Categories: Isocyanates;Nitrogen Compounds;Organic Building Blocks
• Mol File: 3555-94-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 39-40 °C(lit.)
• Flash Point: 40 °F
• Appearance: /
• Density: 0.938 g/mL at 25 °C(lit.)
• Vapor Pressure: 493mmHg at 25°C
• Refractive Index: n20/D 1.4190(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: VINYL ISOCYANATE 97(CAS DataBase Reference)
• NIST Chemistry Reference: VINYL ISOCYANATE 97(3555-94-0)
• EPA Substance Registry System: VINYL ISOCYANATE 97(3555-94-0)

Safety Data

• Hazard Codes: F,T
• Statements: 11-20/21-25-37/38-41-42-43-42/43
• Safety Statements: 16-26-36/37/39-45
• RIDADR: UN 3383 6.1/PG 1
• WGK Germany: 3
• Hazardous Substances Data: 3555-94-0(Hazardous Substances Data)

Usage

General Description

VINYL ISOCYANATE 97 is a chemical compound used in the production of polyurethane foams and elastomers. It is a clear, colorless liquid with a pungent odor and is highly reactive with water and alcohols. Vinyl isocyanate 97 is a potential skin and respiratory irritant, and can cause sensitization upon prolonged or repeated exposure. It is important to handle this chemical with caution and use appropriate personal protective equipment when working with it. Additionally, it is important to follow proper storage and handling procedures to minimize the risk of exposure.

InChI:InChI=1/C3H3NO/c1-2-4-3-5/h2H,1H2

Upstream product

• 50830-56-3 acryloyl azide 
• 814-68-6 acryloyl chloride 
• 28705-47-7 N-tert-Butyl-N-vinylcarbamidsaeurechlorid 
• 127-19-5 N,N-dimethyl acetamide 
• 70008-75-2 α-Chlorethylcarbamidsaeurechlorid 
• 82639-25-6 N-(ethenylcarbamoyl)-4-(diethylamino)-3-methyl-2-pyridinone 
• 72866-46-7 1-Bromethylcarbamidsaeure-bromid 
• 1795-48-8 Isopropyl isocyanate 
• 7150-72-3 t-butyl N-vinylcarbamate 

Downstream Products

• 13370-08-6 allylyrea 
• 101089-70-7 (1-phenylsulfanyl-ethyl)-thiocarbamic acid S-phenyl ester 
• 103151-14-0 N-methyl-N-phenyl-N'-vinyl-urea 
• 7150-72-3 t-butyl N-vinylcarbamate 
• 114158-64-4 Vinylcarbamidsaeure-(4-formyl-phenylester) 
• 99072-16-9 N'-Vinyl-4-carboxy-phenylharnstoff 
• 7418-53-3 p-Phenylen-bis- 
• 138421-66-6 N-ethenyl-2-(pyrrolidin-1-yl)cyclopent-1-enecarboxamide 
• 6504-96-7 1,3,5-triethenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione 
• 1114-51-8 N,N-diethylpropanamide 
• 82639-26-7 4-(diethylamino)-3-methyl-2-pyridinone 
• 82639-27-8 2-(diethylamino)-3-methyl-4-pyridinone 
• 82639-25-6 N-(ethenylcarbamoyl)-4-(diethylamino)-3-methyl-2-pyridinone 
• 1371664-48-0 (S)-1-phenylethyl vinylcarbamothioate 

Relevant articles and documents

A calorimetric investigation to safely scale-up a curtius rearrangement of acryloyl azide

N-Vinyl-O-benzyl urethane was prepared for use as a starting material in a multistep synthesis of a drug candidate. After unsuccessful attempts to employ non-Curtius options to prepare this intermediate, we decided to assess the thermodynamic and kinetic parameters of the acyl azide Curtius rearrangement and trapping of the intermediate isocyanate. (Prepared in analogy to the literature method of Hegedus et al.: Wieber, G. M.; Hegedus, L. S.; Akermark, B.; Michalson, E. T. J. Org. Chem. 1989, 54, 4649-4653.) Reaction calorimetry was utilized to show that the rate of the Curtius rearrangement was completely dose-rate controlled, and that under carefully defined conditions this reaction could be safely performed on limited scale. In addition to addressing the thermal hazard issues, profiling the reaction with reaction calorimetry and interfaced technologies resulted in significant process improvements.

METHOD FOR PRODUCING ACRYLOYL AZIDE

PROBLEM TO BE SOLVED: To provide a method for easily and efficiently producing an acryloyl azide from acrylic acid which may have a substituent at an α-carbon atom or its acid anhydride, and a method for easily and efficiently producing an N-vinylisocyanate and an N-vinylcarbamate from the acryloyl azide. SOLUTION: The method for producing the acryloyl azide is to react the acrylic acid which may have a substituent on the α-carbon atom or its acid anhydride with an azide compound. The method for producing the N-vinyl carbamate is to perform a rearrangement reaction of the acryloyl azide to obtain the N-vinylisocyanate which is reacted with an alcohol.