2,4,6-trimethylaniline

2,4,6-Trimethylaniline is an organic compound with the chemical formula (CH3)3C6H2NH2. This aromatic amine is a colorless liquid, although commercial samples can appear yellowish. It is one of three isomers of trimethylaniline.

Structure and synthesis

2,4,6-Trimethylaniline is a tertiary amine, meaning it has three alkyl groups attached to the nitrogen atom. It is a derivative of aniline, where the hydrogen atoms on the 2, 4, and 6 positions of the benzene ring have been replaced by methyl groups.

The compound can be synthesized by the reaction of aniline with tert-butyl chloride in the presence of a base, followed by deprotection.

Properties

2,4,6-Trimethylaniline is a colorless liquid at room temperature, with a boiling point of 240-242 °C and a melting point of -7 °C. It is slightly soluble in water, but readily soluble in organic solvents such as ethanol and diethyl ether.

Applications

2,4,6-Trimethylaniline is used as a precursor to certain dyes and pigments, including some azo dyes. It is also used in the synthesis of other organic compounds.

Safety

Like many amines, 2,4,6-trimethylaniline is a skin and eye irritant. It is also harmful if swallowed or inhaled. It is not classified as a carcinogen, but it may cause damage to organs through prolonged or repeated exposure.

See also

• Aniline
• Trimethylaniline
• Aromatic amine