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N,N-dimethylaniline
Sign in to saveAlso known as N,N-Dimethylbenzeneamine, N,N-Dimethylphenylamine, N,N-Dimethyl-N-phenylamine, Dimethylphenylamine, Dimethylaniline
'''N,N-Dimethylaniline (DMA''') is an organic chemical compound, a substituted derivative of aniline. It is a tertiary amine, featuring a 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.
Chemical data
- Formula
- C8H11N
- Molecular weight
- 121.18 g/mol
- IUPAC name
- N,N-dimethylaniline
- SMILES
- CN(C)C1=CC=CC=C1
- InChIKey
- JLTDJTHDQAWBAV-UHFFFAOYSA-N
- XLogP
- 2.3
- Polar surface area
- 3.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 121.089149
Show 15 more facts
- chemical formula
- C₈H₁₁N
- solubility
- 2
- immediately dangerous to life or health
- 496
- ionization energy
- 7.12
- NIOSH Pocket Guide ID
- 0223
- density
- 0.96
- melting point
- 2.45
- boiling point
- 194.15
- vapor pressure
- 1
- flash point
- 142
- time-weighted average exposure limit
- 25
- short-term exposure limit
- 50
- canonical SMILES
- CN(C)C1=CC=CC=C1
- Commons category
- N,N-Dimethylaniline
- electric dipole moment
- 1.68
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Preparation
- Reactions
- Applications
- References
'''N,N-Dimethylaniline (DMA') is an organic chemical compound, a substituted derivative of aniline. It is a tertiary amine, featuring a 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== DMA was first reported in 1850 by the German chemist A. W. Hofmann, who prepared it by heating aniline and iodomethane: C6H5NH2 + 2 CH3I → C6H5N(CH3)2 + 2 HI DMA is produced industrially by alkylation of aniline with methanol in the presence of an acid catalyst: C6H5NH2 + 2 CH3OH → C6H5N(CH3)2 + 2 H2O Similarly, it is also prepared using dimethyl ether as the methylating agent. ==Reactions== Dimethylaniline undergoes many of the reactions expected for an aniline, being weakly basic and reactive toward electrophiles.
Excerpted from Wikipedia’s “N,N-dimethylaniline” article, available under the CC BY-SA 4.0 licence.