| |||
| Names | |||
|---|---|---|---|
| Preferred IUPAC name N,N-Dimethylaniline | |||
| Other names DMA Dimethylaminobenzene N,N-Dimethylbenzeneamine N,N-Dimethylphenylamine | |||
| Identifiers | |||
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3D model (JSmol) | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
| ||
| ECHA InfoCard | 100.004.085 | ||
| KEGG |
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| UNII | |||
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| Properties | |||
| C8H11N | |||
| Molar mass | 121.183 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Odor | amine-like | ||
| Density | 0.956 g/mL | ||
| Melting point | 2 °C (36 °F; 275 K) | ||
| Boiling point | 194 °C (381 °F; 467 K) | ||
| 2% (20°C)[1] | |||
| Vapor pressure | 1 mmHg (20°C)[1] | ||
| −89.66·10−6 cm3/mol | |||
| Hazards | |||
| Flash point | 63 °C (145 °F; 336 K) | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) | 1410 mg/kg (rat, oral)[2] | ||
LCLo (lowest published) | 50 ppm (rat, 4 hr)[2] | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) | TWA 5 ppm (25 mg/m3) [skin][1] | ||
REL (Recommended) | TWA 5 ppm (25 mg/m3) ST 10 ppm (50 mg/m3) [skin][1] | ||
IDLH (Immediate danger) | 100 ppm[1] | ||
| Safety data sheet (SDS) | External MSDS | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
N,N-Dimethylaniline (DMA) is anorganic chemical compound, a substituted derivative ofaniline. It is atertiary amine, featuring a dimethylamino group attached to aphenyl group. This oily liquid is colourless when pure, but commercial samples are often yellow. It is an important precursor to dyes such ascrystal violet.
DMA was first reported in 1850 by the German chemistA. W. Hofmann, who prepared it by heating aniline andiodomethane:[3][4]
DMA is produced industrially byalkylation ofaniline withmethanol in the presence of an acid catalyst:[5]
Similarly, it is also prepared usingdimethyl ether as the methylating agent.
Dimethylaniline undergoes many of the reactions expected for an aniline, being weakly basic and reactive toward electrophiles.[6]
It isnitrated to producetetryl, a derivative with fournitro groups which was once used as explosive. In acidic solution, the initial nitration gives 3-nitrodimethylaniline.[7] It reacts withbutyllithium to give the 2-lithio derivative. Electrophilic methylating agents likedimethyl 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 importanttriarylmethane dyes such asmalachite green andcrystal violet.[9] DMA serves as a promoter in the curing of polyester and vinyl ester resins.[10] DMA is also used as a precursor to other organic compounds. A study of the in vitro metabolism ofN,N-dimethylaniline using guinea pig and rabbit preparations and GLC techniques has confirmedN-demethylation andN-oxidation as metabolic pathways, and has also established ring hydroxylation as a metabolic route.[11]
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