General Description
Yellow crystals with an aromatic odor. Sinks in water.
Reactivity Profile
O-NITROCHLOROBENZENE is incompatible with strong bases and strong oxidizing agents. O-NITROCHLOROBENZENE, [LIQUID] will react with ammonia.
Air & Water Reactions
This chemical may be sensitive to prolonged exposure to air and light. Insoluble in water.
Hazard
Toxic by inhalation and ingestion. Combustible. Questionable carcinogen.
Health Hazard
INHALATION: Headache, languour, anemia. Irritation of nose and throat, cyanosis, shallow respiration, convulsions, and coma. EYES: Irritation. SKIN: Irritation. INGESTION: Forms methemoglobin giving rise to cyanosis and blood changes.
Chemical Properties
yellow solid with a characteristic odour
Definition
ChEBI: 1-chloro-2-nitrobenzene is a C-nitro compound that is nitrobenzene in which one of the ortho- hydrogens has been replaced by chlorine. It is a C-nitro compound and a member of monochlorobenzenes.
Production Methods
Nitration of chlorobenzene with mixed acid (30/56/14) typically gives an isomer mix in 98 % yield consisting of 34 – 36 % 2-Nitrochlorobenzene, 63 – 65 % 4- chloronitrobenzene, and only ca. 1 % 3- chloronitrobenzene. The ortho – para ratio of about 0.55 is in sharp contrast to the 1.6 obtained with nitrotoluene isomers. As with the nitration of toluene, much work has been done on isomer control so that the producer might have some flexibility towards the balance of isomer demand. Although no major change in ratio has been achieved, the situation is better for nitrochlorobenzene than nitrotoluenes, because the favored isomer is in much greater demand. In further contrast to the nitration of toluene, the nitration of chlorobenzene in the presence of phosphoric acid decreases the proportion of 4-Nitrochlorobenzene, and the use of phosphoric acid in the presence of a transition-metal catalyst is said to increase the ortho – para ratio to ca. 0.8.
Flammability and Explosibility
Notclassified
Purification Methods
Crystallise it from EtOH, MeOH or pentane (charcoal). [Beilstein 5 IV 721.]