4-Chloro-2-methylaniline

Chemical Properties

clear brown liquid

Chemical Properties

The chloromethylanilines are colorless or white crystalline solids or liquids, some have a mild fishy odor.

Uses

4-Chloro-2-methylaniline may be used in the synthesis of the following:

• 2,8-dichloro-4,10-dimethyl-6H,12H-5,11-methanodibenzo[b,f]-diazocine via reaction with paraformaldehyde in toluene
• N-allylated derivative via palladium-catalyzed selective monoallylation with allyl alcohol
• N-(4-chloro-2-methylphenyl)benzamide via reaction with benzoyl chloride

Uses

Intermediate.

Definition

ChEBI: 4-Chloro-ortho-toluidine is a member of monochlorobenzenes.

General Description

Gray to white solid with a weak fishy odor. Sinks in water. Freezing point is 77°F.

Air & Water Reactions

May be sensitive to prolonged exposure to air and light. Insoluble in water.

Reactivity Profile

4-Chloro-2-methylaniline is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents. . A halogenated amine. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Hazard

Toxic by ingestion and inhalation. Probable carcinogen.

Health Hazard

Inhalation, ingestion, or skin contact causes bluish tint in fingernails, lips, and ears. Headache, drowsiness, and nausea also occur. Contact with eyes causes irritation.

Fire Hazard

Special Hazards of Combustion Products: Toxic oxides of nitrogen and hydrochloric acid fumes may form.

Safety Profile

Confirmed carcinogen. Poison by ingestion and subcutaneous routes. Human mutation data reported. In the presence of copperpI) chloride catalyst decomposition occurs above 239'C. When heated to decomposition it emits toxic fumes of Cland NOx. See also other chloro toluidme entries.

Potential Exposure

Most of the isomers are used in dyestuff manufacture. The 3-chloro-para isomer is used to kill birds. It is marketed as pelleted bait for control of bird populations.

Carcinogenicity

p-Chloro-o-toluidine and its hydrochloride salt are reasonably anticipated to be human carcinogens based on limited evidence of carcinogenicity from studies in humans and evidence of carcinogenicity from studies in experimental animals.

Shipping

UN2239 Chlorotoluidines, solid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3429 Chlorotoluidines, liquid, Hazard Class: 6.1; Labels: 6.1- Poisonous materials

Incompatibilities

Incompatible with oxidizers, strong acids; chloroformates, and acid anhydrides, isocyanates, aldehydes forming fire and explosive hazards.