| Chemical Properties | clear pale yellow to brown liquid with ammonia odor. darkens on exposure to air. almost insoluble in water, soluble in acids and most common organic solvents. |
| Uses | 2-Chloroaniline is the raw material of herbicide green sulfuron, and also an important dye intermediate. It is the color base of ice dyeing dyestuff and can also be used as the diazo component of azo dyestuff to produce acid black, acid blue and organic color precipitation water solid yellow R, permanent red FR, Hansa yellow HR, etc. |
| Uses | 2-Chloroaniline used as petroleum solvents. It is used in biological studies to evaluate the mutagenicity and carcinogenicity of Salmonella typhimurium. Used as a Intermediates for dyestuff, pigment and specialty chemicals. 2-Chloroaniline is widely used in polymer, rubber, pharmaceutical and dye industries. |
| Preparation | The synthesis method of 2-chloroaniline is to reflux 2-nitrochlorobenzene with iron filings, dilute hydrochloric acid and water for 6~8h, distill to get crude product, and then distill to get finished product. |
| Synthesis Reference(s) | The Journal of Organic Chemistry, 39, p. 2718, 1974 DOI: 10.1021/jo00932a011
Tetrahedron Letters, 26, p. 3277, 1985 DOI: 10.1016/S0040-4039(00)98171-1 |
| General Description | Clear amber liquid with an amine odor. Occurs in both alpha and beta forms. |
| Air & Water Reactions | Sensitive to prolonged exposure to air and darkens on exposure to light. Insoluble in water. |
| Reactivity Profile | 2-Chloroaniline is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents. |
| Hazard | Toxic by ingestion. |
| Fire Hazard | 2-Chloroaniline is combustible. |
| Safety Profile | Poison by skin contact,
ingestion, and subcutaneous routes.
Mutation data reported. When heated to
decomposition it emits toxic fumes of Cl
and NOx. See also ANILINE DYES. |
| Purification Methods | Free it from small amounts of the p-isomer by dissolving in one equivalent of H2SO4 and steam distilling. The p-isomer remains behind as the sulfate. [Sidgwick & Rubie J Chem Soc 1013 1921.] An alternative method is to dissolve it in warm 10% HCl (11mL/g of amine) and on cooling, o-chloroaniline hydrochloride separates out. The latter can be recrystallised until the acetyl derivative has a constant melting point (m 90o). (In this way, yields are better than via the recrystallisation of the picrate from EtOH or of the acetyl derivative from pet ether.) [King & Orton J Chem Soc 1377 1911]. [Beilstein 12 III 1281, 12 IV 1115.] |
