N,N-dimethylaniline

N,N-dimethylaniline (DMA) is an organic compound with the formula (CH3)2NC6H5. This colorless liquid is a common precursor in organic synthesis and used in the industrial production of many pharmaceuticals. The compound is a derivative of aniline, consisting of an amine bound to two methyl groups and a phenyl group.

Structure and properties

N,N-dimethylaniline is a tertiary amine, with the nitrogen atom connected to three carbon atoms. It is a weak base, with a pKa of 5.14. The molecule is planar, with the nitrogen atom involved in the aromaticity. This structure is confirmed by X-ray crystallography.

Production

N,N-dimethylaniline is produced by alkylation of aniline with methanol in the presence of a strong acid, such as hydrochloric acid or sulfuric acid. The reaction is as follows:

C6H5NH2 + 2 CH3OH → (CH3)2NC6H5 + 2 H2O

Applications

N,N-dimethylaniline is used as a precursor to other chemicals, including dyes and pharmaceuticals. It is also used as a catalyst in the production of polyurethane foams and epoxy resins.

Safety

Exposure to N,N-dimethylaniline can cause skin and eye irritation, and prolonged exposure can lead to liver and kidney damage. It is classified as a Group 2B carcinogen by the International Agency for Research on Cancer (IARC), meaning it is possibly carcinogenic to humans.

See also

• Aniline
• Methanol
• Organic compound
• Amine
• Methyl
• Phenyl
• pKa
• X-ray crystallography
• Hydrochloric acid
• Sulfuric acid
• Catalyst
• Polyurethane
• Epoxy
• International Agency for Research on Cancer