2,4-Dimethyl aniline

Chemical properties

colourless to yellow or dark brown liquid

The Uses of 2,4-Dimethyl aniline

2,4-Xylidine, as part of the commercial mixture, has the same uses as xylidine.

Definition

ChEBI: A primary arylamine that is aniline in which the hydrogens at the 2- and 4-positions are replaced by methyl groups. A clear to yellow liquid, it is used in production of certain dyes, pesticides and other chemicals.

General Description

Dark brown liquid.

Air & Water Reactions

2,4-Dimethyl aniline may be sensitive to prolonged exposure to air. Slightly soluble in water.

Reactivity Profile

2,4-Dimethyl aniline ignites on contact with fuming nitric acid . Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Fire Hazard

2,4-Dimethyl aniline is combustible.

Safety Profile

Suspected carcinogen. Poison by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also other xylidine entries.

Metabolic pathway

The major urinary metabolite of 2,4-dimethylaniline (2,4-DMA) in rats is N-acetyl-4-amino-3-methylbenzoic acid, while in dogs, it is 6-hydroxy-2,4-dimethylaniline. Dogs also produce a smaller amount of unacetylated 4-amino-3-methylbenzoic acid and its glycine conjugate. 2,6-Dimethylaniline (2,6-DMA) is metabolized principally to 4-hydroxy-2,6- dimethylaniline in both species, but dogs also produce a significant quantity of 2-amino-3-methylbenzoic acid along with a trace amount of the glycine conjugate of the latter metabolite and 2,6-dimethylnitrosobenzene. Trace levels of an unknown postulated to be 3,5- dimethyl-4-iminoquinone are found in dog urine.

Purification Methods

Convert uns-xylidine to a derivative (see below) which, after recrystallisation, is decomposed with alkali to give the free base. Dry it over KOH and fractionally distil. The acetyl derivative has m 130o, the benzoyl derivative has m 192o, and the picrate has m 209o. [Beilstein 12 H 1111, 12 IV 2545.]