1-Chloro-3-nitrobenzene

Chemical properties

Moist tan or pale yellow crystalline solid

The Uses of 1-Chloro-3-nitrobenzene

Intermediate for dyes.

What are the applications of Application

1-Chloro-3-nitrobenzene is used in preparation of aromatic azo compounds

Production Methods

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.

Definition

ChEBI: 1-chloro-3-nitrobenzene is a C-nitro compound that is nitrobenzene in which one of the meta- hydrogens has been replaced by chlorine. It is a C-nitro compound and a member of monochlorobenzenes.

General Description

Pale yellow crystals. Insoluble in water.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

3-Nitrochlorobenzene can react with oxidizing materials. .

Hazard

Toxic by inhalation and ingestion. Combustible. Questionable carcinogen.

Fire Hazard

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

Flammability and Explosibility

Not classified

Safety Profile

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.

Synthesis

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.

Purification Methods

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