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4-Chloroaniline

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4-Chloroaniline Basic information
4-Chloroaniline Chemical Properties
  • Melting point:67-70 °C(lit.)
  • Boiling point:232 °C(lit.)
  • Density 1,43 g/cm3
  • vapor density 4.4 (vs air)
  • vapor pressure 0.15 mm Hg ( 25 °C)
  • refractive index 1.5546
  • Flash point:120°C
  • storage temp. 2-8°C
  • solubility 2.2g/l
  • form Crystalline Solid
  • pka4.15(at 25℃)
  • color Beige to brown-purple
  • Specific Gravity1.2417
  • OdorSweetish
  • PH6.9 (1g/l, H2O, 20℃)
  • PH Range6.9 at 1.00000 g/l at 20 °C
  • Water Solubility 0.3 g/100 mL (20 ºC)
  • Merck 14,2118
  • BRN 471359
  • Henry's Law Constant1.07 at 25 °C (calculated, Howard, 1989)(x 10-5 atm?m3/mol)
  • Stability:Stable. Combustible. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides, chloroformates, nitrous acid. May be light sensitive.
  • CAS DataBase Reference106-47-8(CAS DataBase Reference)
  • NIST Chemistry Referencep-Chloroaniline(106-47-8)
  • EPA Substance Registry Systemp-Chloroaniline (106-47-8)
Safety Information
MSDS
4-Chloroaniline Usage And Synthesis
  • Chemical Properties4-Chloroaniline is a colourless to slightly amber-coloured crystalline solid with a mild aromatic odour. It is Soluble in hot water and organic solvents. 4-Chloroaniline has a moderate vapour pressure and n-octanol/ water partition coefficient. It decomposes in the presence of light and air and at elevated temperatures.
  • Physical propertiesYellowish-white solid with a mild, sweetish odor. Odor threshold concentration is 287 ppm (quoted, Keith and Walters, 1992).
  • Uses4-Chloroaniline(is also called PCA) is used as an intermediate in the production of a number of products, including agricultural chemicals, azo dyes and pigments, cosmetics, and pharmaceutical products.
  • DefinitionChEBI: A chloroaniline in which the chloro atom is para to the aniline amino group.
  • General DescriptionA white or pale yellow solid. Melting point 69.5°C.
  • Air & Water ReactionsInsoluble in cold water. Soluble in hot water [Hawley].
  • Reactivity Profile4-Chloroaniline is incompatible with oxidizing agents. Also incompatible with acids, acid chlorides, acid anhydrides and chloroformates. Subject to exothermic decomposition during high-temperature distillation. Incompatible with nitrous acid.
  • HazardToxic by inhalation and ingestion. Possible carcinogen.
  • Health HazardInhalation or ingestion causes bluish tint to fingernails, lips, and ears indicative of cyanosis; headache, drowsiness, and nausea, followed by unconsciousness. Liquid can be absorbed through skin and cause similar symptoms. Contact with eyes causes irritation.
  • Fire HazardSpecial Hazards of Combustion Products: Irritating and toxic hydrogen chloride and oxides of nitrogen may form in fires.
  • Safety ProfileConfirmed carcinogen with experimental neoplastigenic and tumorigenic data. Poison by ingestion, inhalation, sh contact, subcutaneous, and intravenous routes. A skin and severe eye irritant. Mutation data reported. When heated to decomposition it emits toxic fumes of Cland NOx. See also ANILINE DYES
  • Environmental FateBiological. In an anaerobic medium, the bacteria of the Paracoccus sp. converted 4- chloroaniline to 1,3-bis(p-chlorophenyl)triazene and 4-chloroacetanilide with product yields of 80 and 5%, respectively (Minard et al., 1977). In a field experiment, [14C]4-chloroaniline was applied to a soil at a depth of 10 cm. After 20 wk, 32.4% of the applied amount was recovered in soil. Metabolites identified include 4-chloroformanilide, 4-chloroacetanilide, 4-chloronitrobenzene, 4- chloronitrosobenzene, 4,4′-dichloroazoxybenzene, and 4,4′-dichloroazobenzene (Freitag et al., 1984).
    Soil. 4-Chloroaniline covalently bonds with humates in soils to form quinoidal structures followed by oxidation to yield a nitrogen-substituted quinoid ring. A reaction half-life of 13 min was determined with one humic compound (Parris, 1980). Catechol, a humic acid monomer, reacted with 4-chloroaniline yielding 4,5-bis(4-chlorophenylamino)-3,5-cyclohexadiene-1,2-dione (Adrian et al., 1989).
    Photolytic. Under artificial sunlight, river water containing 2–5 ppm 4-chloroaniline photodegraded to 4-aminophenol and unidentified polymers (Mansour et al., 1989). Photooxidation of 4-chloroaniline (100 μM) in air-saturated water using UV light (λ >290 nm) produced 4-chloronitrobenzene and 4-chloronitrosobenzene. About 6 h later, 4-chloroaniline completely reacted leaving dark purple condensation products (Miller and Crosby, 1983). In a similar study, irradiation of an aqueous solution in the range of 290–350 nm resulted in the formation of the intermediate 4-iminocyclohexa-2,5-dienylidene (Othmen et al., 2000). A carbon dioxide yield of 27.7% was achieved when 4-chloroaniline adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985).
    A rate constant of 8.3 x 10-11 cm3/molecule?sec was reported for the gas-phase reaction of 4- chloroaniline and OH radicals in air (Wahner and Zetzsch, 1983).
    Chemical/Physical. 4-Chloroaniline will not hydrolyze to any reasonable extent (Kollig, 1993).
    Pizzigallo et al. (1998) investigated the reaction of 4-chloroaniline with ferric oxide and two forms of manganese dioxide [birnessite (δ-MnO2) and pyrolusite (MnO2)] within the pH range of 4–8 at 25 °C. The reaction rate of 4-chloroaniline was in the order birnessite > pyrolusite > ferric oxide. At pH 4.0, the reaction with birnessite was so rapid that the reaction could not be determined. Half-lives for the reaction of 4-chloroaniline with pyrolusite and ferric oxide were 383 and 746 min, respectively. The reaction rate decreased as the pH was increased. The only oxidation compounds identified by GC/MS were 4,4′-dichloroazobenzene and 4-chloro-4′- hydroxydiphenylamine.
  • Purification MethodsCrystallise the aniline from MeOH, pet ether (b 30-60o), or 50% aqueous EtOH, then *benzene/pet ether (b 60-70o), and then dry it in a vacuum desiccator. It can be distilled under vacuum (b 75-77o/3mm). It sublimes in a very high vacuum. The acetate crystallises from aqueous MeOH (m 178o, 180o) or EtOH or AcOH (m 173-174o) and has b 331.3o/760mm. [Beilstein 12 III 1325, 12 IV 1116.]
4-Chloroaniline Preparation Products And Raw materials
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