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Dimethylaniline
Chemical compound From Wikipedia, the free encyclopedia
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N,N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. It is a tertiary amine, featuring a dimethylamino group attached to a phenyl group. This oily liquid is colourless when pure, but commercial samples are often yellow. It is an important precursor to dyes such as crystal violet.
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Preparation
DMA was first reported in 1850 by the German chemist A. W. Hofmann, who prepared it by heating aniline and iodomethane:[3][4]
- C6H5NH2 + 2 CH3I → C6H5N(CH3)2 + 2 HI
DMA is produced industrially by alkylation of aniline with methanol in the presence of an acid catalyst:[5]
- C6H5NH2 + 2 CH3OH → C6H5N(CH3)2 + 2 H2O
Similarly, it is also prepared using dimethyl ether as the methylating agent.
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Reactions
Dimethylaniline undergoes many of the reactions expected for an aniline, being weakly basic and reactive toward electrophiles.[6]
It is nitrated to produce tetryl, a derivative with four nitro groups which was once used as explosive. In acidic solution, the initial nitration gives 3-nitrodimethylaniline.[7] It reacts with butyllithium to give the 2-lithio derivative. Electrophilic methylating agents like dimethyl sulfate attack the amine to give the quaternary ammonium salt:[8]
- C6H5N(CH3)2 +(CH3O)2SO2 → C6H5N(CH3)3CH3OSO3
Diethylaniline and dimethylaniline are both used as acid-absorbing bases.
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Applications
DMA is a key precursor to commercially important triarylmethane dyes such as malachite green and crystal violet.[9] DMA serves as a promoter in the curing of polyester and vinyl ester resins.[10] DMA is also used as a precursor to other organic compounds. A study of the in vitro metabolism of N,N-dimethylaniline using guinea pig and rabbit preparations and GLC techniques has confirmed N-demethylation and N-oxidation as metabolic pathways, and has also established ring hydroxylation as a metabolic route.[11]
References
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