Chemical Properties
clear yellow-brown to brown liquid
Uses
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. This compound was also employed to produce 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.]
