1-ХЛОРО-3-НИТРОБЕНЗОЛ

Химические свойства

Moist tan or pale yellow crystalline solid

Использование

Intermediate for dyes. 1-Chloro-3-nitrobenzene was used in the preparation of aromatic azo compounds using gold (Au) nanoparticles supported on TiO2 as a catalyst. It was also used as surrogate standard to evaluate the removal of 2,4-dinitrotoluene from contaminated soils using enhanced electrokinetic remediation.

Методы производства

m-Chloronitrobenzene is of lesser economic importance than its ortho- and para-isomers, with no U.S. production reported. The annual production in Germany was reported to be on the order of 1000–3000 metric tons. It has limited use in the manufacturing of dyes and agricultural chemicals.
There is no information on potential exposure. Chloronitrobenzene has been detected in the surface water of the Rhine River with concentrations between 20 and 500 ng/L and in fish at levels of up to 1 mg/kg.

Общее описание

Pale yellow crystals. Insoluble in water.

Реакции воздуха и воды

Insoluble in water.

Профиль реактивности

3-Nitrochlorobenzene can react with oxidizing materials. .

Опасность

Toxic by inhalation and ingestion. Combustible. Questionable carcinogen.

Пожароопасность

Flash point data for 3-Nitrochlorobenzene are not available. 3-Nitrochlorobenzene is probably combustible.

Профиль безопасности

Poison by ingestion and inhalation. It forms methemoglobin in the body and gves rise to cyanosis and blood changes. Its effects are cumulative and analogous to those of nitrobenzene. The para compound is thought to be somewhat less toxic than the ortho compound. Chemically, it is probably converted in the body to chloroaniline, whch is also poisonous. In industry, it is the dust of hs material that is most often the source of intoxication. Flammable liquid and dangerous fire hazard when exposed to heat or flame. It can react with oxidizing materials. When heated to decomposition it emits toxic fumes of Cl-, NOx, and phosgene. See also other chloronitrobenzene entries and NITRO COMPOUNDS of AROMATIC HYDROCARBONS.

Синтез

1-Chloro-3-nitrobenzene was synthesised from 4-chloro-2-nitro-benzoic acid by adding copper iodide, triethylamine and dimethyl sulfoxide in the presence of inert gas using the Schlenk technique.

Методы очистки

Crystallise the nitrobenzene from MeOH or 95% EtOH (charcoal), then pentane. [Beilstein 5 IV 722.]