Dimethylaniline

N,N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline.

DMA was first reported in 1850 by the German chemist A. W. Hofmann, who prepared it by heating aniline and iodomethane:[3][4] DMA is produced industrially by alkylation of aniline with methanol in the presence of an acid catalyst:[5] Similarly, it is also prepared using dimethyl ether as the methylating agent.

Dimethylaniline undergoes many of the reactions expected for an aniline, being weakly basic and reactive toward electrophiles.

Electrophilic methylating agents like dimethyl sulfate attack the amine to give the quaternary ammonium salt:[8] Diethylaniline and dimethylaniline are both used as acid-absorbing bases.

DMA is a key precursor to commercially important triarylmethane dyes such as malachite green and crystal violet.

Skeletal formula of dimethylaniline
Ball-and-stick model of the dimethylaniline molecule