Appearance Colorless liquid Density 956 kg/m³ Molar mass 121.19 g/mol | Formula C8H11N Boiling point 194 °C Melting point 2 °C | |
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N,N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. It consists of a tertiary amine, featuring 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.
Contents
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Preparation and reactions
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DMA was first reported in 1850 by the German chemist A. W. Hofmann, who prepared it by heating aniline and iodomethane:
C6H5NH2 + 2 CH3I → C6H5N(CH3)2 + 2 HIDMA is produced industrially by alkylation of aniline with methanol in the presence of an acid catalyst:
C6H5NH2 + 2 CH3OH → C6H5N(CH3)2 + 2 H2OSimilarly, it is also prepared using dimethyl ether as the methylating agent.
![Dimethylaniline 26Dimethylaniline 99 SigmaAldrich](https://alchetron.com/cdn/dimethylaniline-7ca2d6e8-406a-48bf-90c6-06c83bacb39-resize-750.jpg)
Dimethylaniline undergoes many of the reactions expected for an aniline, being weakly basic and reactive toward electrophiles. For example, it is nitrated to produce tetryl, a derivative with four nitro groups which was once used as explosive. It is lithiated with butyllithium. Methylating agents attack the amine to give the quaternary ammonium salt:
C6H5N(CH3)2 + (CH3O)2SO2 → C6H5N(CH3)3CH3OSO3Applications
![Dimethylaniline 35Dimethylaniline 98 SigmaAldrich](https://alchetron.com/cdn/dimethylaniline-02b70588-c586-4498-a861-250f7b37bc7-resize-750.jpg)
DMA is a key precursor to commercially important triarylmethane dyes such as malachite green and crystal violet. DMA serves as a promoter in the curing of polyester and vinyl ester resins. 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. Its derivative 2,4-dimethylaniline is a recalcitrant degradant of the pesticide amitraz and is also an industrial pollutant which is genotoxic, teratogenic and carcinogenic.
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