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Dimethylamine is a weak base and the pKa of the ammonium CH 3-NH + 2 -CH 3 is 10.73, a value above methylamine (10.64) and trimethylamine (9.79). Dimethylamine reacts with acids to form salts, such as dimethylamine hydrochloride, an odorless white solid with a melting point of 171.5 °C.
DMA is prepared commercially by the reaction of dimethylamine with acetic anhydride or acetic acid. Dehydration of the salt of dimethylamine and acetic acid also furnishes this compound: [5] CH 3 CO 2 H·HN(CH 3) 2 → H 2 O + CH 3 CON(CH 3) 2. Dimethylacetamide can also be produced by the reaction of dimethylamine with methyl acetate. [6]
DMA was first reported in 1850 by the German chemist A. W. Hofmann, who prepared it by heating aniline and iodomethane: [3] [4]. C 6 H 5 NH 2 + 2 CH 3 I → C 6 H 5 N(CH 3) 2 + 2 HI. DMA is produced industrially by alkylation of aniline with methanol in the presence of an acid catalyst: [5]
Methylamine has been produced industrially since the 1920s (originally by Commercial Solvents Corporation for dehairing of animal skins). [4] This was made possible by Kazimierz Smoleński [] and his wife Eugenia who discovered amination of alcohols, including methanol, on alumina or kaolin catalyst after WWI, filed two patent applications in 1919 [5] and published an article in 1921.
N,N-Dimethylethylamine (DMEA), sometimes referred to as dimethylethylamine, is an organic compound with formula (CH 3) 2 NC 2 H 5.It is an industrial chemical that is mainly used in foundries as a catalyst for epoxy resins and polyurethane as well as sand core production.
Melting point: −61.00 °C; −77.80 °F; 212.15 K ... Because it is bulky, it is a more selective nucleophile than other similar amines, such as dimethylamine. [5]
Dimethylethanolamine (DMAE or DMEA) is an organic compound with the formula (CH 3) 2 NCH 2 CH 2 OH.It is bifunctional, containing both a tertiary amine and primary alcohol functional groups.
It undergoes directed ortho metalation with butyl lithium: [C 6 H 5 CH 2 N(CH 3) 2 + BuLi → 2-LiC 6 H 4 CH 2 N(CH 3) 2 LiC 6 H 4 CH 2 N(CH 3) 2 + E + → 2-EC 6 H 4 CH 2 N(CH 3) 2. Via these reactions, many derivatives are known with the formula 2-X-C 6 H 4 CH 2 N(CH 3) 2 (E = SR, PR 2, etc.).