View source for Dimethylaniline

{{About|N,N-dimethylaniline|other constitutional isomers|xylidine}}
{{chembox
| verifiedrevid = 306956124
| Name = ''N'',''N''-Dimethylaniline
| ImageFile = Dimethylaniline.png
| ImageSize = 100px
| IUPACName = ''N'',''N''-Dimethylaniline
| OtherNames = DMA
| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite}}
| CASNo = 121-69-7
| PubChem =
| SMILES = CN(C)c1ccccc1}}
| Section2 = {{Chembox Properties
| Formula =  C<sub>8</sub>H<sub>11</sub>N
| MolarMass = 121.19 g/mol
| Appearance = colourless liquid
| Density = 0.956 g/mL
| MeltingPt = 2 °C
| BoilingPt = 194 °C
| Solubility = }}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt = 63 °C
| ExternalMSDS = [http://www.jtbaker.com/msds/englishhtml/d6040.htm External MSDS]
| Autoignition = }}
}}

'''''N'',''N''-Dimethylaniline''' (DMA) is an [[organic compound|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]].

==Preparation and reactions==
DMA was first reported in 1850 by A. W. Hofmann, who prepared it by heating aniline and [[iodomethane]]:{{Fact|date=October 2008}}
:C<sub>6</sub>H<sub>5</sub>NH<sub>2</sub>  +  2 CH<sub>3</sub>I   →   C<sub>6</sub>H<sub>5</sub>N(CH<sub>3</sub>)<sub>2</sub> + 2 [[hydrogen iodide|HI]] <!-- probably the aniline serves as base also-->
DMA is produced industrially by [[alkylation]] of aniline with [[methanol]] in the presence of an acid catalyst:<ref name=Ullmann>Thomas Kahl, Kai-Wilfrid Schröder, F. R. Lawrence, W. J. Marshall, Hartmut Höke, Rudolf Jäckh "Aniline" in Ullmann's Encyclopedia of Industrial Chemistry 2007; John Wiley & Sons: New York.{{DOI|10.1002/14356007.a02_303}}</ref>
:C<sub>6</sub>H<sub>5</sub>NH<sub>2</sub>  +  2 [[methanol|CH<sub>3</sub>OH]]  →  C<sub>6</sub>H<sub>5</sub>N(CH<sub>3</sub>)<sub>2</sub>  +  2 H<sub>2</sub>O
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. For example, it is [[nitration|nitrated]] to produce [[tetryl]], a derivative with four [[nitro compound|nitro]] groups which was once used as explosive.  It is lithiated with [[n-Butyllithium|butyllithium]]. Methylating agents attack the amine to give the quaternary ammonium salt:<ref>{{OrgSynth | | author = J. Jacques and A. Marquet | title = Selective α-Bromination of an Aralkyl Ketone with Phenyltrimethylammonium Tribromide: 2-Bromoacetyl-6-methoxynaphthalene and 2,2-Dibromoacetyl-6-Methoxynaphthalene | collvol = 6 | collvolpages = 175 | year = 1988 | prep = CV6P0175}}</ref>
:C<sub>6</sub>H<sub>5</sub>N(CH<sub>3</sub>)<sub>2</sub>  +  [[dimethyl sulfate|(CH<sub>3</sub>O)<sub>2</sub>SO<sub>2</sub>]]  →  C<sub>6</sub>H<sub>5</sub>N(CH<sub>3</sub>)<sub>3</sub>CH<sub>3</sub>OSO<sub>3</sub>

==Applications==
DMA is a key precursor to commercially important [[triarylmethane dye]]s such as [[Malachite green]] and [[Crystal violet]].<ref>Thomas Gessner and Udo Mayer "Triarylmethane and Diarylmethane Dyes" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim.{{DOI|10.1002/14356007.a27_179}}</ref>  DMA serves as a promoter in the curing of polyester and vinyl ester resins.<ref>[http://www.compositesaustralia.com.au/dma.htm General Info on DMA (N,N-Dimethylaniline)], Composites Australia</ref>  DMA is also used as a precursor to other organic compounds.

==References==
{{reflist}}

[[Category:Aromatic amines]]

[[ar:ثنائي ميثيل الأنيلين]]
[[de:N,N-Dimethylanilin]]
[[et:N,N-dimetüülaniliin]]
[[fr:Diméthylaniline]]
[[lv:N,N-dimetilanilīns]]
[[nl:N,N-dimethylaniline]]
[[ja:ジメチルアニリン]]
[[pl:Dimetyloanilina]]
[[pt:Dimetilanilina]]
[[ru:Диметиланилин]]
[[sk:Dimetylanilín]]
[[fi:N,N-dimetyylianiliini]]
[[sv:Dimetylanilin]]
[[zh:N,N-二甲基苯胺]]
[[Category:2Fix]]