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2,4,6-Trichlorophenol

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2,4,6-Trichlorophenol Basic information
2,4,6-Trichlorophenol Chemical Properties
  • Melting point:64-66 °C(lit.)
  • Boiling point:246 °C(lit.)
  • Density 1.49
  • vapor pressure 1 mm Hg ( 76.5 °C)
  • refractive index 1.5300 (estimate)
  • Flash point:99 °C
  • storage temp.  0-6°C
  • solubility 0.8g/l
  • pka6.15 (Leuenberger et al., 1985)
    6.10 (Blackman et al., 1955)
    6.0 (Eder and Weber, 1980)
  • form Crystalline Mass or Crystalline Powder and Chunks
  • color white to slightly brown
  • Water Solubility 0.8 g/L
  • Merck 14,9644
  • BRN 776729
  • Henry's Law Constant9.07 at 25 °C (estimated, Leuenberger et al., 1985a)
  • CAS DataBase Reference88-06-2(CAS DataBase Reference)
  • IARC2B (Vol. 117) 2019
  • NIST Chemistry ReferencePhenol, 2,4,6-trichloro-(88-06-2)
  • EPA Substance Registry System2,4,6-Trichlorophenol (88-06-2)
Safety Information
MSDS
2,4,6-Trichlorophenol Usage And Synthesis
  • Description2,4,6-Trichlorophenol is a colorless to yellow solid that has a strong phenol-like smell. It decomposes at elevated temperatures when heated to produce corrosive and toxic fumes including chlorine and hydrogen chloride. It is soluble in organic solvents and partially soluble in water.
    Previously, it was used in the manufacture of other chemicals. Moreover, it was also used as an antiseptic, a pesticide for leather, wood, and preservation of glue as well as an anti-mildew treatment. Nevertheless, the production of 2,4,6-Trichlorophenol was discontinued in America in the 1980s.
  • Health EffectsHuman beings may be exposed to 2,4,6-Trichlorophenol via inhalation and can cause altered pulmonary functions, respiratory effects, and pulmonary lesions. Moreover, 2,4,6-trichlorophenol can irritate the lungs and throat causing coughing and wheezing. In animal models, ingestion of 2,4,6-trichlorophenol caused an increase in occurrences of leukemia, lymphoma, and liver cancer. As such, 2,4,6-Trichlorophenol might be a carcinogenic in humans.
    Contact can severely burn and irritate the eyes and skin with possible eye damage. Elevated exposures may cause weakness, restlessness, rapid breathing, shaking, tremors, coma, seizures, or even death.
    Extreme exposure to 2,4,6-trichlorophenol can have devastating effect on a developing fetus. Other long-term effect to repeated exposure may cause bronchitis with shortness of breath.
  • Chemical PropertiesYellow flakes; strong phenolic odor. Soluble in acetone, alcohol, and ether; insoluble in water. Nonflammable.
  • Physical propertiesColorless needles or yellow solid with a strong, phenolic, musty or rotten vegetable-type odor. At 40 °C, the lowest concentration at which an odor was detected was 380 μg/L. At 25 °C, the lowest concentration at which a taste was detected was >12 μg/L (Young et al., 1996).
  • UsesWood preservative; disinfectant; fungicide, herbicide, defoliant.
  • UsesFungicide, herbicide, defoliant.
  • DefinitionChEBI: A trichlorophenol with phenolic substituents on positions 2, 4 and 6.
  • Synthesis Reference(s)The Journal of Organic Chemistry, 24, p. 1523, 1959 DOI: 10.1021/jo01092a034
  • Air & Water ReactionsInsoluble in water.
  • Reactivity Profile2,4,6-Trichlorophenol is incompatible with acid chlorides, acid anhydrides and oxidizing agents. 2,4,6-Trichlorophenol can be converted to the sodium salt by reaction with sodium carbonate. Forms ethers, esters and salts by reaction with metals and amines. Undergoes substitution reactions such as nitration, alkylation, acetylation and halogenation. Can be hydrolyzed by reaction with bases at elevated temperatures and pressures. Reacts with alkalis at high temperatures .
  • Health HazardIn experimental animals, 2,4,6- trichlorophenol causes toxic effects to the liver and hematologic system and cancer. There is no reliable information regarding exposure and toxic effects in humans.
  • Fire HazardLiterature sources indicate that 2,4,6-Trichlorophenol is nonflammable.
  • Safety ProfileConfirmed carcinogen with experimental carcinogenic data. Poison by intraperitoneal route. Moderately toxic by ingestion and skin contact. A skin and severe eye irritant. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl-. Used as a germicide and preservative. See also CHLOROPHENOLS.
  • Carcinogenicity2,4,6-Trichlorophenol is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
  • Environmental FateBiological. In activated sludge, only 0.3% mineralized to carbon dioxide after 5 d (Freitag et al., 1985). In anaerobic sludge, 2,4,6-trichlorophenol degraded to 4-chlorophenol (Mikesell and Boyd, 1985). When 2,4,6-trichlorophenol was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, significant biodegradation with rapid adaptation was observed. At concentrations of 5 and 10 mg/L, 96 and 97% biodegradation, respectively, were observed after 7 d (Tabak et al., 1981).
    Photolytic. Titanium dioxide suspended in an aqueous solution and irradiated with UV light (λ = 365 nm) converted 2,4,6-trinitrophenol to carbon dioxide at a significant rate (Matthews, 1986). A carbon dioxide yield of 65.8% was achieved when 2,4,6-trichlorophenol adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985).
    Chemical/Physical. An aqueous solution containing chloramine reacted with 2,4,6-trichlorophenol to yield the following intermediate products after 2 h at 25 °C: 2,6-dichloro-1,4- benzoquinone-4-(N-chloro)imine and 4,6-dichloro-1,2-benzoquinone-2-(N-chloro)imine (Maeda et al., 1987).
  • Purification MethodsCrystallise the phenol from *benzene, EtOH or EtOH/water. [Beilstein 6 IV 1005.]
2,4,6-Trichlorophenol Preparation Products And Raw materials
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