ABSTRACT
CASRN: 88-74-4; DOT: 1661; DOT label: Poison; molecular formula: C6H6N2O2; FW: 138.13; RTECS: BY6650000; Merck Index: 12, 6680 Physical state, color, and odor: Orange-yellow crystals with a musty odor Melting point (°C): 71.45 (Gross et al., 1933) 69.3 (Collett and Johnston, 1926) Boiling point (°C): 284.1 (Dean, 1973) Density (g/cm3): 1.442 at 15 °C (Weast, 1986) 0.9015 at 25 °C (Sax, 1984) 1.44 at 20 °C (Weiss, 1986) Diffusivity in water (x 10-5 cm2/sec): 0.78 at 20 °C using method of Hayduk and Laudie (1974) Dissociation constant, pKa: 13.25 (quoted, Keith and Walters, 1992) Flash point (°C): 168 (Hawley, 1981) Lower explosive limit (%): Not pertinent (Weiss, 1986) Entropy of fusion (cal/mol⋅K): 11.2 (Domalski and Hearing, 1998) Heat of fusion (kcal/mol): 3.85 (Tsonopoulos and Prausnitz, 1971)
5.88 at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999) Bioconcentration factor, log BCF: 0.91 (Brachydanio rerio, Kalsch et al., 1991) Ionization potential (eV): 8.27, 8.43, 8.66 (Mallard and Linstrom, 1998) Soil organic carbon/water partition coefficient, log Koc: 1.23-1.62 using method of Karickhoff et al. (1979) Octanol/water partition coefficient, log Kow: 1.44 at 25 °C (shake flask-UV spectrophotometry, Fujita et al., 1964) 1.79 (quoted, Leo et al., 1971) 1.73 (Kramer and Henze, 1990) 1.83 (shake flask-GLC, Hansch and Anderson, 1967) Solubility in organics: In g/kg: benzene (208 at 25 °C), chloroform (11.7 at 0 °C), and ethanol (278.7 at 25 °C) (Collett and Johnston, 1926) Solubility in water: 1.0 g/L at 30 °C (Phatak and Gaikar, 1996) 1.47 g/L at 30 °C (shake flask-interferometer, Gross et al., 1933) 1.212 and 2.423 g/kg at 25 and 40 °C, respectively (shake flask-titration, Collett and Johnston,
1926) Vapor pressure (mmHg): 8.1 at 25 °C (Mabey et al., 1982) 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-(2amino-3-nitrophenyl)glucopyranoside, and β-(4-amino-3-nitrophenyl)-glucopyranoside (Pogány et al., 1990). Toxicity: EC50 (15-min) for Photobacterium phosphoreum 26.9 mg/L (Yuan and Lang, 1997). IC50 (24-h) for river bacteria 34.7 mg/L (Yuan and Lang, 1997). Acute LD50 for wild birds 750 mg/kg, guinea pigs 2,350 mg/kg, mice 1,070 mg/kg, quail 750 mg/kg, rats 1,600 mg/kg (quoted, RTECS, 1985). Use: Organic synthesis.
