General Description
Orange solid with a musty odor. Sinks and mixes slowly with water.
Reactivity Profile
O-NITROANILINE(88-74-4) may be sensitive to prolonged exposure to light. Mixtures of this chemical with magnesium are hypergolic on contact with nitric acid. O-NITROANILINE(88-74-4) forms extremely explosive addition compounds with hexanitroethane. O-NITROANILINE(88-74-4) has a vigorous reaction with sulfuric acid above 392° F. O-NITROANILINE(88-74-4) is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizers.
Air & Water Reactions
Insoluble in water.
Hazard
Explosion risk. Toxic when absorbed by
skin.
Health Hazard
Inhalation or ingestion causes headache, nausea, methemo-globinemia, vomiting, weakness, and stupor; cyanosis caused by contact usually develops in 4-6 hrs.; prolonged and excessive exposure may also cause liver damage. Contact with eyes or skin causes irritation; continued exposure may cause same symptoms as inhalation or ingestion.
Fire Hazard
Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire.
Chemical Properties
orange solid
Uses
2-Nitroaniline is the main precursor to?phenylenediamines, which are converted to?benzimidazoles, a family of?heterocycles?that are key components in pharmaceuticals.
Uses
Dyestuff intermediate.
Synthesis Reference(s)
Journal of the American Chemical Society, 77, p. 5688, 1955
DOI: 10.1021/ja01626a066Organic Syntheses, Coll. Vol. 1, p. 388, 1941
Environmental Fate
Biological. Under aerobic and anaerobic conditions using a sewage inoculum, 2-nitroaniline
degraded to 2-methylbenzimidazole and 2-nitroacetanilide (Hallas and Alexander, 1983). A
Pseudomonas sp. strain P6, isolated from a Matapeake silt loam, did not grow on 2-nitroaniline as
the sole source of carbon. However, in the presence of 4-nitroaniline, approximately 50% of the
applied 2-nitroaniline metabolized to nonvolatile products which could not be identified by HPLC
(Zeyer and Kearney, 1983). In activated sludge inoculum, following a 20-d adaptation period, no
degradation was observed (Pitter, 1976).
Plant. 2-Nitroaniline was degraded by tomato cell suspension cultures (Lycopericon
lycopersicum). Transformation products identified were 2-nitroanilino-β-D-glucopyranoside, β-(2-
amino-3-nitrophenyl)glucopyranoside, and β-(4-amino-3-nitrophenyl)-glucopyranoside (Pogány et
al., 1990).
Purification Methods
Crystallise the aniline from hot water (charcoal), then from aqueous 50% EtOH, or EtOH, and dry it in a vacuum desiccator. It has also been chromatographed on alumina, then recrystallised from *benzene. [Beilstein 12 IV 1563.]
