3,5-Dimethylaniline

Chemical properties

clear yellow-brown to brown liquid

The Uses of 3,5-Dimethylaniline

3,5-Dimethylaniline is the reagent commonly useful in the manufacture of dyes. It undergoes polymerization in the presence of cerium(IV) sulfate as an oxidant. 3,5-Dimethylaniline was used in the synthesis of chiral packing materials for high performance liquid chromatography.

General Description

Dark brown liquid.

Air & Water Reactions

3,5-Dimethylaniline may be sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

3,5-XYLIDINE ignites on contact with fuming nitric acid (NTP, 1992). 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

3,5-Dimethylaniline is combustible.

Safety Profile

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

Purification Methods

Convert sym-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 it. The acetyl derivative has m 144o, the benzoyl derivative has m 136o and the picrate has m 209o (from H2O, EtOH or 10% AcOH). [Beilstein 12 H 1131, 12 IV 2561.]