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| 2,4,5-Trichlorophenol Basic information |
| 2,4,5-Trichlorophenol Chemical Properties |
Melting point | 64-67 °C
67-69 °C (lit.) | Boiling point | 248 °C/740 mmHg (lit.) | density | 1,678 g/cm3 | vapor pressure | 3.5 at 8 °C, 22 at 25 °C (quoted, Leuenberger et al., 1985a) | refractive index | 1.5300 (estimate) | Fp | 253°C | storage temp. | 2-8°C | solubility | Soluble in ethanol and ligroin (U.S. EPA, 1985) | pka | pK1:7.37 (25°C) | form | Powder | color | Colorless needles or gray flakes from pet ether | Odor | strong phenolic odor | Water Solubility | 947.8mg/L(25 ºC) | Merck | 14,9643 | BRN | 607569 | Henry's Law Constant | 1.76 at 25 °C (estimated, Leuenberger et al., 1985a) | Stability: | Stable. Note that this material creates dioxin in alkaline media at elevated temperatures. | CAS DataBase Reference | 95-95-4(CAS DataBase Reference) | NIST Chemistry Reference | Phenol, 2,4,5-trichloro-(95-95-4) | EPA Substance Registry System | 2,4,5-Trichlorophenol (95-95-4) |
| 2,4,5-Trichlorophenol Usage And Synthesis |
Chemical Properties | White to pale brown solid in appearance; 2,4,5-Trichlorophenol also looks like small needles. It has a really strong odor that smells like phenol (a poisonous crystal-looking compound). This man-made substance is not found naturally in the environment. | Physical properties | Colorless crystals or yellow to gray flakes with a strong, disinfectant or phenolic odor. At 40 °C,
the average odor threshold concentration and the lowest concentration at which an odor were
detected were 350 and 63 μg/L, respectively. At 25 °C, the lowest concentration at which a taste
was detected was 100 μg/L (Young et al., 1996). | Uses | 2,4,5-Trichlorophenol is used as a broad range pesticide against insects, fungi, vegetation and bacteria. It has become a common environmental contaminant and probable human carcinogen. | Preparation | 2,4,5-Trichlorophenol is prepared indirectly, by the alkaline hydrolysis of 1,2,4,5-tetrachlorobenzene,because the direct chlorination of 2,5-dichlorophenol, difficult to achieve, proceeds with poor yield. | Definition | ChEBI: 2,4,5-trichlorophenol is a trichlorophenol carrying chloro groups at positions 2, 4 and 5. | General Description | Colorless needles, gray flakes or off-white lumpy solid. Phenolic odor. Formerly used as a fungicide and bactericide. | Air & Water Reactions | Insoluble in water. | Reactivity Profile | 2,4,5-Trichlorophenol is a weak monobasic acid. Incompatible with acid chlorides, acid anhydrides and oxidizing agents. Produces dioxin in alkaline medium at high temperatures | Health Hazard | If your skin comes into contact with 2,4,5-trichlorophenol, it may burn the skin and produce redness and edema in humans. It also irritates the eyes, nose, pharynx, and lungs in humans. Tests involving acute exposure of rats, mice, and guinea pigs have demonstrated 2,4,5-trichlorophenol to havemoderateacute toxicity by oral exposure. | Fire Hazard | Literature sources indicate that 2,4,5-Trichlorophenol is nonflammable. | Safety Profile | Suspected carcinogen
with experimental neoplastigenic data.
Poison by intraperitoneal and intravenous
routes. Moderately toxic by ingestion and
subcutaneous routes. Experimental
reproductive effects. Mutation data
reported. When heated to decomposition it
emits toxic fumes of Cland explodes. See
also CHLOROPHENOLS. | Environmental fate | Biological. Chloroperoxidase, a fungal enzyme isolated from Caldariomyces fumago,
chlorinated 2,4,5-trichlorophenol to give 2,3,4,6-tetrachlorophenol (Wannstedt et al., 1990).
Photolytic. When 2,4,5-trichlorophenol (100 μM) in an oxygenated, titanium dioxide (2 g/L)
suspension was irradiated by sunlight (λ ≥340 nm), complete mineralization to carbon dioxide and
water and chloride ions was observed (Barbeni et al., 1987a).
The following phototransformation half-lives were reported for 2,4,5-trichlorophenol in
estuarine water exposed to sunlight and microbes: 1 h during winter; in distilled water: 0.6 and 1 h
during summer and winter, respectively; in poisoned estuarine water: 14 and 24 h during summer
and winter, respectively (Hwang et al., 1986).
A photooxidation rate constant of <3,000/M·sec was reported for the reaction of 2,4,5-
trichlorophenol and ozone in water at a pH range of 1.2 to 1.5 (Hoigné and Bader, 1983).
Chemical/Physical. 2,4,5-Trichlorophenol will not hydrolyze because it does not contain a
hydrolyzable functional group (Kollig, 1993).
During the manufacture/synthesis of 2,4,5-T using alkalies at high temperatures, some TCDD
may form (Worthing and Hance, 1991). | Purification Methods | Crystallise the phenol from EtOH or pet ether. [Beilstein 6 IV 962.] |
| 2,4,5-Trichlorophenol Preparation Products And Raw materials |
Raw materials | Sodium hydroxide-->Sulfuric acid-->Toluene-->Sodium dithionite-->Propylene glycol-->Sodium tetraborate-->1,2,4,5-Tetrachlorobenzene-->1,2,3,5-Tetrachlorobenzene-->CARBONIC ACID TERT-BUTYL 2,4,5-TRICHLOROPHENYL ESTER-->2,3,4,6-TETRACHLOROPHENOL | Preparation Products | Hexachlorophene-->2,4,5-Trichlorophenyl-propynyl ether-->HALOPROGIN-->FENCHLORPHOS-->Butanoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-(ethoxymethylphosphinyl)-, (2S)- (9CI)-->FENCHLORPHOS-OXON-->2,5-DICHLOROHYDROQUINONE-->Trimethyl phosphate-->2,4,5-Trichlorophenoxyacetic acid-->2,3,6-TRICHLOROPHENOL |
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