''N'',''N''-Dimethylaniline (DMA) is an

organic chemical compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon chemical bond, bonds. Due to carbon's ability to Catenation, catenate (form chains with other carbon atoms), millions of organic c ...

, a substituted derivative of

aniline Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile starti ...

. It consists of a

tertiary amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such ...

, featuring dimethylamino group attached to a

phenyl In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen ...

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 Crystal violet or gentian violet, also known as methyl violet 10B or hexamethyl pararosaniline chloride, is a triarylmethane dye used as a histological stain and in Gram's method of classifying bacteria. Crystal violet has antibacterial, antif ...

Preparation and reactions

DMA was first reported in 1850 by the German chemist A. W. Hofmann, who prepared it by heating aniline and

iodomethane Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one ...

: :C₆H₅NH₂ + 2 CH₃I → C₆H₅N(CH₃)₂ + 2 HI DMA is produced industrially by

alkylation Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecti ...

with methanol in the presence of an acid catalyst:Kahl, Thomas ''et al.'' (2007) "Aniline" in ''Ullmann's Encyclopedia of Industrial Chemistry''. John Wiley & Sons: New York. :C₆H₅NH₂ + 2 CH₃OH → C₆H₅N(CH₃)₂ + 2 H₂O Similarly, it is also prepared using

dimethyl ether Dimethyl ether (DME; also known as methoxymethane) is the organic compound with the formula CH3OCH3, (sometimes ambiguously simplified to C2H6O as it is an isomer of ethanol). The simplest ether, it is a colorless gas that is a useful precursor ...

as the methylating agent. 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 2,4,6-Trinitrophenylmethylnitramine commonly referred to as tetryl ( C7 H5 N5 O8) is an explosive compound used to make detonators and explosive booster charges. Tetryl is a nitramine booster explosive, though its use has been largely superseded ...

, a derivative with four

nitro Nitro may refer to: Chemistry *Nitrogen, a chemical element and a gas except at very low temperatures, with which many compounds are formed: **Nitro compound, an organic compound containing one or more nitro functional groups, -NO2 **Nitroalkene, ...

groups which was once used as explosive. It is lithiated with

butyllithium Butyllithium may refer to one of 5 isomeric organolithium reagents of which 3 are commonly used in chemical synthesis: * ''n''-Butyllithium, abbreviated BuLi or nBuLi * ''sec''-Butyllithium, abbreviated ''sec''-BuLi or sBuLi, has 2 stereoisomers, ...

. Methylating agents attack the amine to give the quaternary ammonium salt: :C₆H₅N(CH₃)₂ + (CH₃O)₂SO₂ → C₆H₅N(CH₃)₃CH₃OSO₃

Applications

DMA is a key precursor to commercially important

triarylmethane dye Triarylmethane dyes are synthetic organic compounds containing triphenylmethane backbones. As dyes, these compounds are intensely colored. They are produced industrially as dyes. Families Triarylmethane dyes can be grouped into families accordin ...

s such as

malachite green Malachite green is an organic compound that is used as a dyestuff and controversially as an antimicrobial in aquaculture. Malachite green is traditionally used as a dye for materials such as silk, leather, and paper. Despite its name the dye is ...

and

. 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.

References

{{reflist Anilines Dimethylamino compounds