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2-Nitroaniline

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2-Nitroaniline Basic information
2-Nitroaniline Chemical Properties
  • Melting point:70-73 °C(lit.)
  • Boiling point:284 °C(lit.)
  • Density 1,255 g/cm3
  • vapor pressure 8.1 at 25 °C (Mabey et al., 1982)
  • refractive index 1.6349 (estimate)
  • Flash point:168 °C
  • storage temp. 2-8°C
  • solubility methanol: 0.1 g/mL, clear
  • pka-0.26(at 25℃)
  • form Crystals or Flakes
  • Colour Index 37025
  • color Orange to brown
  • PH6.1 (10g/l, H2O, 20℃)(slurry)
  • Water Solubility 1.1 g/L (20 ºC)
  • Merck 14,6582
  • BRN 509275
  • Henry's Law Constant5.88 x 10-8 atm?m3/mol at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999)
  • Stability:Stable. Incompatible with acids, acid chlorides, acid anhydrides, strong oxidizing agents, chloroformates, hexanitroethane.
  • CAS DataBase Reference88-74-4(CAS DataBase Reference)
  • NIST Chemistry Referenceo-Nitroaniline(88-74-4)
  • EPA Substance Registry Systemo-Nitroaniline (88-74-4)
Safety Information
MSDS
2-Nitroaniline Usage And Synthesis
  • Chemical Propertiesorange solid
  • UsesDyestuff intermediate.
  • Synthesis Reference(s)Journal of the American Chemical Society, 77, p. 5688, 1955 DOI: 10.1021/ja01626a066
    Organic Syntheses, Coll. Vol. 1, p. 388, 1941
  • General DescriptionOrange solid with a musty odor. Sinks and mixes slowly with water.
  • Air & Water ReactionsInsoluble in water.
  • Reactivity Profile2-Nitroaniline may be sensitive to prolonged exposure to light. Mixtures of 2-Nitroaniline with magnesium are hypergolic on contact with nitric acid. 2-Nitroaniline forms extremely explosive addition compounds with hexanitroethane. 2-Nitroaniline has a vigorous reaction with sulfuric acid above 392° F. 2-Nitroaniline is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizers.
  • HazardExplosion risk. Toxic when absorbed by skin.
  • Health HazardInhalation 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 HazardSpecial Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire.
  • Safety ProfileA poison. Moderately toxic by ingestion. Mildly toxic by skin contact. Mutation data reported. Mixtures with magnesium are hypergolic on contact with nitric acid. Forms extremely explosive addltion compounds with hexanitroethane. Vigorous reaction with sulfuric acid above 200°C. When heated to decomposition it emits toxic fumes of NOx. See also m- NITROANILINE, p-NITROANILINE, and ANILINE DYES.
  • Environmental FateBiological. 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 MethodsCrystallise 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.]
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