Dimethylaniline: Difference between revisions

| verifiedrevid = 443691340

| ImageFile = Dimethylaniline.png

| ImageSize = 100px

| IUPACName = ''N'',''N''-Dimethylaniline

| OtherNames = DMA

| Section1 = {{Chembox Identifiers

| ChEMBL = 371654

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| CASNo_Ref = {{cascite}}

| Section2 = {{Chembox Properties

| Formula = C₈H₁₁N

| MolarMass = 121.19 g/mol

| Appearance = colourless liquid

| MeltingPt = 2 °C

| BoilingPt = 194 °C

| Solubility = }}

| Section3 = {{Chembox Hazards

| FlashPt = 63 °C

| ExternalMSDS = [http://hazard.com/msds/mf/baker/baker/files/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]].

DMA was first reported in 1850 by A. W. Hofmann, who prepared it by heating aniline and [[iodomethane]]:{{Fact|date=October 2008}}

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>

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>

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.

[[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]]