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2-Chloroaniline

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2-Chloroaniline Basic information
2-Chloroaniline Chemical Properties
  • Melting point:0-3 °C
  • Boiling point:208-210 °C(lit.)
  • Density 1.213 g/mL at 25 °C(lit.)
  • vapor density 4.41 (vs air)
  • vapor pressure 0.5 hPa (20 °C)
  • refractive index n20/D 1.589
  • Flash point:98 °C
  • storage temp. Store below +30°C.
  • solubility water: soluble5.13g/L at 20°C
  • form Liquid
  • pka2.65(at 25℃)
  • color Clear pale yellow to brown
  • OdorCharacteristic odour
  • explosive limit2.4-14.2%(V)
  • Water Solubility 5.13 g/L (20 ºC)
  • Merck 14,2118
  • BRN 606077
  • CAS DataBase Reference95-51-2(CAS DataBase Reference)
  • NIST Chemistry Referenceo-Chloroaniline(95-51-2)
  • EPA Substance Registry Systemo-Chloroaniline (95-51-2)
Safety Information
MSDS
2-Chloroaniline Usage And Synthesis
  • Chemical Propertiesclear pale yellow to brown liquid
  • UsesDye intermediate, standards for colorimetric apparatus, manufacture of petroleum solvents and fungicides.
  • Synthesis Reference(s)The Journal of Organic Chemistry, 39, p. 2718, 1974 DOI: 10.1021/jo00932a011
    Tetrahedron Letters, 26, p. 3277, 1985 DOI: 10.1016/S0040-4039(00)98171-1
  • General DescriptionClear amber liquid with an amine odor. Occurs in both alpha and beta forms.
  • Air & Water ReactionsSensitive to prolonged exposure to air and darkens on exposure to light. Insoluble in water.
  • Reactivity Profile2-Chloroaniline is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents.
  • HazardToxic by ingestion.
  • Fire Hazard2-Chloroaniline is combustible.
  • Safety ProfilePoison by skin contact, ingestion, and subcutaneous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl and NOx. See also ANILINE DYES.
  • Purification MethodsFree it from small amounts of the p-isomer by dissolving in one equivalent of H2SO4 and steam distilling. The p-isomer remains behind as the sulfate. [Sidgwick & Rubie J Chem Soc 1013 1921.] An alternative method is to dissolve it in warm 10% HCl (11mL/g of amine) and on cooling, o-chloroaniline hydrochloride separates out. The latter can be recrystallised until the acetyl derivative has a constant melting point (m 90o). (In this way, yields are better than via the recrystallisation of the picrate from EtOH or of the acetyl derivative from pet ether.) [King & Orton J Chem Soc 1377 1911]. [Beilstein 12 III 1281, 12 IV 1115.]
2-Chloroaniline Preparation Products And Raw materials
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