Identifiers | |
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3D model (JSmol)
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ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C2H5N | |
Molar mass | 43.069 g·mol−1 |
Related compounds | |
Related compounds
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dimethylamine Methanimine Ethanimine |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N-Methylmethanimine or N‐methyl methylenimine is a reactive molecular substance containing a methyl group attached to an imine. It can be written as CH3N=CH2. On a timescale of minutes it self reacts to form the trimer trimethyl 1,3,5-triazinane. N-Methylmethanimine is formed naturally in the Earth's atmosphere, by oxidation of dimethylamine and trimethylamine, both of which are produced by animals, or burning.[1]
N-Methylmethanimine can be produced in two steps from dimethylamine, by first chlorinating the nitrogen atom with solid N-chlorosuccinimide, and then treating with potassium tert-butoxide at 90°C.[2] Also it can be formed directly by thermal decomposition.[3]
It can also be prepared from the trimer: 1,3,5-trimethyl-1,3,5-triazinane by heating to 450 °C (842 °F).[2]
At 515 °C (959 °F), trimethylamine decomposes into methane and N-methylmethanimine.[4]
N-Methylmethanimine should be formed in the atmosphere as a result of degradation by oxidation of di- and trimethylamine. These occur at concentrations of a few parts per billion. But N-methylmethanimine cannot be detected. This is likely because it forms the trimer, gets absorbed onto particles, such as cloud droplets, and hydrolyses to form methylamine and formaldehyde.[1]
The N-Methylmethanimine molecule has Cs symmetry.[2] The infrared spectrum and microwave spectrum have been observed.[5]
The bond length for C=N is 1.279 Å, and for the N-C bond it is 1.458 Å. The ∠ C=N-C is 116.6°.[4]
The electric dipole moment is 1.53 Debye.[6]
When heated to 535°, N-methylmethanimine decomposes to hydrogen cyanide (HCN) and methane (CH4).[4]
Between 400 and 550°C, the cyclic amine, aziridine decomposes to a mixture of N-methylmethanimine and ethylideneimine.[7]