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2-Chlorophenol

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2-Chlorophenol Basic information
2-Chlorophenol Chemical Properties
  • Melting point:8 °C(lit.)
  • Boiling point:175-176 °C(lit.)
  • Density 1.241 g/mL at 25 °C(lit.)
  • vapor pressure 13.3 hPa (50 °C)
  • refractive index n20/D 1.558(lit.)
  • Flash point:147 °F
  • storage temp.  0-6°C
  • solubility alcohol: freely soluble
  • form neat
  • pka8.49(at 25℃)
  • Water Solubility 28.5 g/L (20 ºC)
  • Merck 14,2154
  • BRN 1905114
  • Henry's Law Constant6.44 x 10-6 atm?m3/mol at 20 °C (Sheikheldin et al., 2001)
  • Stability:Stable. Hygroscopic. Combustible. Incompatible with oxidizing agents, acid anhydrides, acid chlorides.
  • InChIKeyISPYQTSUDJAMAB-UHFFFAOYSA-N
  • CAS DataBase Reference95-57-8(CAS DataBase Reference)
  • NIST Chemistry Reference2-Chlorophenol(95-57-8)
  • EPA Substance Registry Systemo-Chlorophenol (95-57-8)
Safety Information
MSDS
2-Chlorophenol Usage And Synthesis
  • Chemical Properties2-Chlorophenol is a colourless to light brown liquid, All isomers have a characteristic odor. It is used to make dyes and other chemicals, and as a disinfectant, bactericide, and germicide.
  • Physical propertiesPale amber liquid with a slight phenolic, floral, or musty-type odor. At 40 °C, the average and lowest odor concentrations detected were 0.36 and 0.088 μg/L, respectively. At 25 °C, the average taste threshold concentration and the lowest concentration at which a taste was detected were 0.97 and 0.94 μg/L, respectively (Young et al., 1996).
  • Uses2-chlorophenol and 2,4-dichlorophenol are used in organic synthesis. 2-chlorophenol is utilized in the manufacture of dye-stulfs and in the process for extracting sulphur and nitrogen compounds from coal.
  • Preparation0.5 mole of tert-butyl hypochlorite is dropped, with stirring, into a solution or suspension of the 0.5 mole of phenol in 150-300 ml of carbon tetrachloride, the temperature being allowed to rise to the boiling point of the solvent. The mixture is then boiled under reflux for a further 2 hours, the carbon tetrachloride and the tert-butyl alcohol are distilled off, and the residue is fractionated collecting fraction boiling at 174.9 °C.
    Preparation of 2-chlorophenol
  • Synthesis Reference(s)The Journal of Organic Chemistry, 35, p. 528, 1970 DOI: 10.1021/jo00827a060
    Tetrahedron Letters, 29, p. 1319, 1988 DOI: 10.1016/S0040-4039(00)80287-7
  • General DescriptionA colorless to amber liquid with an unpleasant, penetrating odor. Density 1.265 g / cm3. Sinks in water and slowly dissolves. Freezing point 7°C (46°F). Boiling point 175°C (347°F).
  • Air & Water ReactionsVery soluble in water
  • Reactivity Profile2-Chlorophenol is a weak acid. Neutralizes bases in exothermic reactions. Incompatible with oxidizing agents. Incompatible with acid chlorides and acid anhydrides. Forms ethers, esters and salts with metals and amines .
  • HazardToxic by skin absorption, inhalation, or ingestion. Strong irritant to tissue.
  • Health HazardPoisonous; may be fatal if inhaled, swallowed or absorbed through skin. Irritating to skin and eyes; direct contact may cause burns. Rats receiving lethal doses via oral, subcutaneous or intraperitoneal routes displayed similar symptoms: restlessness, increased breathing rate and motor weakness followed by tremors, chronic convulsions, dyspnea, coma and death.
  • Safety ProfilePoison by ingestion, intraperitoneal, and intravenous routes. Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. Flammable liquid when exposed to heat, flame, or oxidizers. To fight fire, use alcohol foam. When heated to decomposition it emits toxic fumes of Cl-. See also CHLOROPHENOLS and CHLORIDES.
  • Potential ExposureMonochlorophenols are used in the manufacture of fungicides, slimicides, bactericides, pesticides, herbicides, disinfectants, wood and glue preservatives; in the production of phenolic resins; in the extraction of certain minerals from coal; as a denaturant for ethanol; as an antiseptic; as a disinfectant, and others.
  • ShippingUN 2020 (solid); UN2021 (liquid) Chlorophenols, solid and liquid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
  • Purification MethodsPass 2-chlorophenol at least twice through a gas chromatography column. It has also been purified by fractional distillation. [Beilstein 6 IV 782.]
  • IncompatibilitiesMay form explosive mixture with air. Contact with oxidizing agents can cause fire and explosion hazard. Heat produces hydrogen chloride and chlorine. Corrosive to aluminum, copper and other chemically active metals.
  • Waste DisposalIncinerate in admixture with flammable solvent in furnace equipped with afterburner and scrubber.
2-Chlorophenol Preparation Products And Raw materials
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