38239-27-9

Basic information

• Product Name: N-Methylenevinylamine
• Synonyms: 2-Azabutane-1,3-diene;N-Methyleneethenamine;N-Methylenevinylamine
• CAS NO: 38239-27-9
• Molecular Formula: C3H5N
• Molecular Weight: 55.0785
• Mol File: 38239-27-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 36.2°Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 0.66g/cm³
• Vapor Pressure: 508mmHg at 25°C
• Refractive Index: 1.377
• PKA: 4.80±0.50(Predicted)
• CAS DataBase Reference: N-Methylenevinylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methylenevinylamine(38239-27-9)
• EPA Substance Registry System: N-Methylenevinylamine(38239-27-9)

Safety Data

• Hazardous Substances Data: 38239-27-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C3H5N/c1-3-4-2/h3H,1-2H2

Upstream product

• 503-29-7 azetidine 
• 32115-53-0 N-chloroazetidine 
• 99337-39-0 N-(chloro-2 ethyl) aminoacetonitrile 
• 118691-53-5 N,N-(trimethylsiloxy-2 ethyl) trimethylsilylaminoacetonitrile 
• 6788-85-8 1-azetine 

Relevant articles and documents

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A Study of the Thermal Decomposition and Dehydrochlorination of N-Chloroazetidine: Microwave Spectra of N-Chloromethylenimine, 1-Azetine, and 2-Azabutadiene

The microwave spectrum of N-chloromethylenimine and 1-azetine has been observed following pyrolysis and dehydrochlorination of N-chloroazetidine, respectively.In addition, pyrolysis of 1-azetine gives another unstable molecule, 2-azabutadiene.The rotational constants determined are A=62434.90(10), B=6676.389(13), and C=6022.843(11) MHz for N-chloromethylenimine, A=62344.73(11), B=6531.700(13), and C=5904.017(11) MHz for the 37Cl species of N-chloromethylenimine, A=13911.630(24), B=12713.799(24), and C=7254.990(24) MHz for 1-azetine, and A=47186.010(23),B=4886.5325(27), and C=4430.0673(23) MHz for 2-azabutadiene.The dipole moments and nuclear quadrupole coupling constants have also been determined from analysis of the spectra.The molecular constants estimated by ab initio MO calculations have been found to be consistent with the experimental results.

Gasphase Reactions, 61. - Cycloalkanimines 2H-Azirine, 1-Azetidine, 1-Pyrroline, 1-Piperideine, and 3,4,5,6-Tetrahydro-2H-azepine: Preparation and Photoelectron Spectra

For preparation of the easily oligomerizing cycloalkanimines , the following gasphase reactions are optimized PE spectroscopically: for the three membered ring imine, 2H-azirine, the heterogeneous KOR dehydrochlorination of the 2-chloroethyl azide preceding the thermolysis of the resulting vinyl azide, and for the lager rings, 1-azetine (n=2), 1-pyrroline (n=3), 1-piperideine (n=4) as well as the seven-membered 3,4,5,6-tetrahydro-2H-azepine, the consecutive chlorination of the corresponding cycloalkylamine over solid N-chlorosuccinimide followed by KOR dehydrochlorination of the N-chloro derivative formed.The PE spectra of all cyclic alkanimines prepared are assigned based on geometry-optimized MNDO calculations, and their electronic structures are discussed by molecular state comparison with increasing ring size and with the isoelectronic series of the cycloalkenes.The thermal ring opening of 1-azetine to 2-azabutadiene is investigated by PE spectroscopic real-time gas analysis; its ionization pattern is assigned by comparison with other azabutadienes.