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2,4-Dichlorophenol

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2,4-Dichlorophenol Basic information
2,4-Dichlorophenol Chemical Properties
  • Melting point:42-43 °C(lit.)
  • Boiling point:209-210 °C(lit.)
  • Density 1.383
  • vapor pressure 1.3 hPa (50 °C)
  • refractive index 1.4430 (estimate)
  • Flash point:237 °F
  • storage temp. 2-8°C
  • solubility methanol: soluble1g in 10ml
  • pkapK1:7.85 (25°C)
  • form melt
  • color White to beige
  • Water Solubility 4.5 g/L (20 ºC)
  • Merck 14,3072
  • BRN 742467
  • Henry's Law Constant2.88 x 10-6 atm?m3/mol at 20 °C (Sheikheldin et al., 2001) 3.23 x 10-6 atm?m3/mol at 25 °C (estimated, Leuenberger et al., 1985a)
  • InChIKeyHFZWRUODUSTPEG-UHFFFAOYSA-N
  • CAS DataBase Reference120-83-2(CAS DataBase Reference)
  • NIST Chemistry ReferencePhenol, 2,4-dichloro-(120-83-2)
  • EPA Substance Registry System2,4-Dichlorophenol (120-83-2)
Safety Information
MSDS
2,4-Dichlorophenol Usage And Synthesis
  • Chemical Propertieswhite to beige crystalline solid
  • Chemical Properties2,4-DCP is a colorless crystalline solid with a characteristic odor
  • Physical propertiesColorless to yellow crystals with a sweet, musty, or medicinal odor. At 40 °C, the average odor threshold concentration and the lowest concentration at which an odor was detected were 29 and 5.4 μg/L, respectively. Similarly, at 25 °C, the average taste threshold concentration and the lowest concentration at which a taste was detected were 2.5 and 0.98 μg/L, respectively (Young et al., 1996).
  • Uses2,4-Dichlorophenol is a chlorinated derivative of phenol and is used as an intermediate for the preparation of herbicide 2,4-dichlorophenoxyacetic acid (D435680).
  • UsesIntermediate in production of herbicidal chlorophenoxy acids such as 2,4- dichlorophenoxyacetic acid
  • DefinitionChEBI: A dichlorophenol that is phenol carrying chloro substituents at positions 2 and 4.
  • Synthesis Reference(s)Synthetic Communications, 20, p. 2991, 1990 DOI: 10.1080/00397919008051517
  • General DescriptionColorless crystalline solid with a medicinal odor. Melting point 45°C. Sinks in water. Strong irritant to tissues; toxic by ingestion.
  • Air & Water ReactionsInsoluble in water.
  • Reactivity Profile2,4-Dichlorophenol can react vigorously with oxidizing agents. Can also react with acids or acid fumes. Incompatible with acid chlorides and acid anhydrides.
  • Health HazardTremors, convulsions, shortness of breath, inhibition of respiratory system.
  • Safety ProfileSuspected carcinogen with experimental carcinogenic and teratogenic data. Poison by intraperitoneal route. Moderately toxic by ingestion and subcutaneous routes. An experimental teratogen. Mutation data reported. Combustible when exposed to heat or flame. Can react vigorously with oxidizing materials. To fight fre, use alcohol foam, foam, CO2, dry chemical. When heated to decomposition, or on contact with acid or acid fumes, it emits hghly toxic fumes of Cl-. See also CHLOROPHENOLS.
  • Potential Exposure2,4-Dichlorophenol is a commercially produced substituted phenol used in the manufacture of industrial and agricultural products; in synthesis of pharmaceuticals. As an intermediate in the chemical industry, 2,4-DCP is utilized as the feedstock for the manufacture of 2,4-dichlorophenoxyacetic acid (2,4-D), and 2,4-D derivatives (germicides, soil sterilants, etc.); certain methyl compounds used in mothproofing, antiseptics and seed disinfectants. 2,4-DCP is also reacted with benzene sulfonyl chloride to produce miticides or further chlorinated to pentachlorophenol, a wood preservative. It is thus a widely used pesticide intermediate. The only group expected to be at risk for high exposure to 2,4-DCP is industrial workers involved in the manufacturing or handling of 2,4-DCP and 2,4-D
  • CarcinogenicityIn mammalian cells in vitro 2,4-DCP produced chromosomal aberrations and induced unscheduled DNA synthesis; it was negative for sister chromatid exchange in vivo and was mostly negative in bacterial assays.
    Oral exposure of pregnant rats to 750mg/kg/day for 10 gestational days induced slightly decreased fetal weight, delayed ossification of sternal and vertebral arches, and some early embryonic deaths.10 Maternal deaths also occurred at this dose, indicating that 2,4-DCP was not selectively toxic to embryos or fetuses. No effects were noted in dams or offspring exposed at 375mg/kg/day.
    A threshold limit value (TLV) has not been established for 2,4-dichlorophenol.
  • Environmental FateBiological. In activated sludge, 2.8% mineralized to carbon dioxide after 5 d (Freitag et al., 1985). In freshwater lake sediments, anaerobic reductive dechlorination produced 4-chlorophenol (Kohring et al., 1989). Chloroperoxidase, a fungal enzyme isolated from Caldariomyces fumago, converted 9 to 12% of 2,4-dichlorophenol to 2,4,6-trichlorophenol (Wannstedt et al., 1990). When 2,4-dichlorophenol 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, 100 and 99% biodegradation, respectively, were observed after 7 d (Tabak et al., 1981). In activated sludge inoculum, 98.0% COD removal was achieved. The average rate of biodegradation was 10.5 mg COD/g?h (Pitter, 1976).
    Surface Water. Hoigné and Bader (1983) reported 2,4-dichlorophenol reacts with ozone at a rate constant of <1,500/M?sec at the pH range of 1.5 to 3.0.
    Groundwater. Nielsen et al. (1996) studied the degradation of 2,4-dichlorophenol in a shallow, glaciofluvial, unconfined sandy aquifer in Jutland, Denmark. As part of the in situ microcosm study, a cylinder that was open at the bottom and screened at the top was installed through a cased borehole approximately 5 m below grade. Five liters of water was aerated with atmospheric air to ensure aerobic conditions were maintained. Groundwater was analyzed weekly for approximately 3 months to determine 2,4-dichlorophenol concentrations with time. The experimentally determined first-order biodegradation rate constant and corresponding half-life were 0.20/d and 3.47 d, respectively.
    Photolytic. In distilled water, photolysis occurs at a slower rate than in estuarine waters containing humic substances. Photolysis products identified in distilled water were the three isomers of chlorocyclopentadienic acid. The following half-lives were reported for 2,4- dichlorophenol in estuarine water exposed to sunlight and microbes: 0.6 and 2.0 h during summer (24 °C) and winter (10 °C), respectively; in distilled water: 0.8 and 3.0 h during summer and winter, respectively; in poisoned estuarine water: 0.7 and 2.0 h during summer and winter, respectively (Hwang et al., 1986). When titanium dioxide suspended in an aqueous solution was irradiated with UV light (λ = 365 nm), 2,4-dichlorophenol was converted to carbon dioxide at a significant rate (Matthews, 1986). An aqueous solution containing hydrogen peroxide and irradiated by UV light (λ = 296 nm) converted 2,4-dichlorophenol to chlorohydroquinone and 1,4- dihydroquinone (Moza et al., 1988). A carbon dioxide yield of 50.4% was achieved when 2,4- dichlorophenol adsorbed on silica gel was irradiated with UV light (λ >290 nm) for 17 h (Freitag et al., 1985).
    Chemical/Physical. 2,4-Dichlorophenol will not hydrolyze to any reasonable extent (Kollig, 1993). Reported second-order rate constants for the reaction of 2,4-dichlorophenol and singlet oxygen in water at 292 K: 7 x 106/M?sec at pH 5.5, 2 x 106/M?sec at pH 6, 1.0 x 105/M?sec at pH 6.65, 1.5 x 106/M?sec at pH 7.0, 7.6 x 105/M?sec at pH 7.9, 1.20 x 104/M?sec at pH 9.0 to 9.6. At pH 8, the half-life of 2,4-dichlorophenol is 62 h (Scully and Hoigné, 1987). In an aqueous phosphate buffer at 27 °C, 2,4-dichlorophenol reacted with singlet oxygen at a rate of 5.1 x 106/M?sec (Tratnyek and Hoigné, 1991). At neutral pH, 2,4-dichlorophenol was completely oxidized by potassium permanganate (2.0 mg/L) after 15 min (quoted, Verschueren, 1983).
  • ShippingUN2020 Chlorophenols, solid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials
  • Purification MethodsCrystallise it from pet ether (b 30-40o). Purify it also by repeated zone melting, using a P2O5 guard tube to exclude moisture. It is very hygroscopic when dry. [Beilstein 6 IV 885.]
  • IncompatibilitiesIncompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, and epoxides. Contact with acids or acid fumes causes decomposition releasing poisonous chlorine gas. Incompatible with caustics, acid anhydrides; acid chlorides. Quickly corrodes aluminum; slowly corrodes zinc, tin, brass, bronze, copper and its alloys. May accumulate static electrical charges, and may cause ignition of its vapors.
  • Waste DisposalDissolve in a combustible solvent and incinerate in a furnace equipped with afterburner and scrubber. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≧100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal
2,4-Dichlorophenol Preparation Products And Raw materials
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