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| | 1,2,3,4-Tetrachlorobenzene Basic information |
| Product Name: | 1,2,3,4-Tetrachlorobenzene | | Synonyms: | 1,2,3,4-tcb;1,2,3,4-tetrachloro-benzen;1,2,3,4-Tetrachlorobenzene in methanol;1,2,3,4-TETRACHLOROBENZENE;1,2,3,4-Tetrachlorobenzene,98%;NSC 50729;1,2,3,4-four chlorobenzene;1.2.3.4-Tetrac | | CAS: | 634-66-2 | | MF: | C6H2Cl4 | | MW: | 215.89 | | EINECS: | 211-214-0 | | Product Categories: | Pesticides&Metabolites;Q-ZAlphabetic;Alpha Sort;TA - TE;T-ZAlphabetic;Volatiles/ Semivolatiles;Aryl;C6;Halogenated Hydrocarbons;Canada;International Standards;Single Component Standards for MISA AnalysesVolatiles/ Semivolatiles;Organics | | Mol File: | 634-66-2.mol |  |
| | 1,2,3,4-Tetrachlorobenzene Chemical Properties |
| Melting point | 44 °C | | Boiling point | 254 °C761 mm Hg(lit.) | | density | 1,73 g/cm3 | | vapor pressure | 1.5 (extrapolated from vapor pressures determined at higher temperatures, Tesconi andYalkowsky, 1998) | | refractive index | 1.5348 (estimate) | | Fp | >230 °F | | storage temp. | APPROX 4°C
| | solubility | 0.0028g/l | | form | neat | | color | White crystals or needles | | Water Solubility | 5.92mg/L(25 ºC) | | BRN | 1910025 | | Henry's Law Constant | 3.6 at 10 °C (Koelmans et al., 1999) | | CAS DataBase Reference | 634-66-2(CAS DataBase Reference) | | EPA Substance Registry System | 1,2,3,4-Tetrachlorobenzene (634-66-2) |
| | 1,2,3,4-Tetrachlorobenzene Usage And Synthesis |
| Chemical Properties | WHITE CRYSTALLINE SOLID | | Uses | Component of dielectric fluids, synthesis. | | Uses | 1,2,3,4-tetrachlorobenzene was used as a model compound to determine the chlorobenzenes (CBs) in soil samples. It was also used for rapid dechlorination of 1,2,3,4-tetrachlorodibenzo-p-dioxin (1,2,3,4-TeCDD). | | Definition | ChEBI: A tetrachlorobenzene carrying chloro groups at positions 1, 2 , 3 and 4. | | General Description | White to off-white crystals. | | Air & Water Reactions | Insoluble in water. | | Reactivity Profile | Simple aromatic halogenated organic compounds, such as 1,2,3,4-Tetrachlorobenzene, are very unreactive. Reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Materials in this group may be incompatible with strong oxidizing and reducing agents. Also, they may be incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides. | | Health Hazard | ACUTE/CHRONIC HAZARDS: 1,2,3,4-Tetrachlorobenzene may cause irritation of the skin. | | Fire Hazard | 1,2,3,4-Tetrachlorobenzene is probably combustible. | | Safety Profile | Moderately toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Irritant. Combustible liquid. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORINATED HYDROCARBONS, AROMATIC. | | Environmental fate | Biological. A mixed culture of soil bacteria or a Pseudomonas sp. transformed 1,2,3,4-
tetrachlorobenzene to 2,3,4,5-tetrachlorophenol (Ballschiter and Scholz, 1980). After incubation in
sewage sludge for 32 d under anaerobic conditions, 1,2,3,4-tetrachlorobenzene did not biodegrade
(Kirk et al., 1989). The half-life of 1,2,3,4-tetrachlorobenzene in an anaerobic enrichment culture
was 26.4 h (Beurskens et al., 1993). Potrawfke et al. (1998) reported that a pure culture of
Pseudomonas chlororaphis RW71 mineralized 1,2,3,4-tetrachlorobenzene as a sole source of
carbon and energy. Intermediate biodegradation products identified were tetrachlorocatechol,
tetrachloromuconic acid, 2,3,5-trichlorodienelactone, 2,3,5-trichloro-4-hydroxymuconic acid.
In an enrichment culture derived from a contaminated site in Bayou d’Inde, LA, 1,2,4,5-
tetrachlorobenzene underwent reductive dechlorination yielding 1,2,4-trichlorobenzene. The
maximum dechlorination rate, based on the recommended Michaelis-Menten model, was 208
nM/d (Pavlostathis and Prytula, 2000).
Photolytic. Irradiation (λ ≥285 nm) of 1,2,3,4-tetrachlorobenzene (1.1–1.2 mM/L) in an
acetonitrile-water mixture containing acetone (0.553 mM/L) as a sensitizer gave the following
products (% yield): 1,2,3-trichlorobenzene (9.2), 1,2,4-trichlorobenzene (32.6), 1,3-dichlorobenzene
(5.2), 1,4-dichlorobenzene (1.5), 2,2′,3,3′,4,4′,5-heptachlorobiphenyl (2.52), 2,2′,3,3′,4,5,6′-
heptachlorobiphenyl (1.22), 10 hexachlorobiphenyls (3.50), five pentachlorobiphenyls (0.87),
dichlorophenyl cyanide, two trichloroacetophenones, trichlorocyanophenol, (trichlorophenyl)
acetonitriles, and 1-(trichlorophenyl)-2-propanone (Choudhry and Hutzinger, 1984). Without
acetone, the identified photolysis products (% yield) included 1,2,3-trichlorobenzene (7.8), 1,2,4-
trichlorobenzene (26.8), 1,2-dichlorobenzene (0.5), 1,3-dichlorobenzene (0.7), 1,4-dichloro-benzene
(30.4), 1,2,3,5-tetrachlorobenzene (2.26), 1,2,4,5-tetrachlorobenzene (0.72), 2,2′,3,3′,4,4′,5-
heptachlorobiphenyl (<0.01), and 2,2′,3,3′,4,5,6′-heptachlorobiphenyl (<0.01) (Choudhry and
Hutzinger, 1984). The sunlight irradiation of 1,2,3,4-tetrachlorobenzene (20 g) in a 100-mL
borosilicate glass-stoppered Erlenmeyer flask for 56 d yielded 4,280 ppm heptachlorobiphenyl
(Uyeta et al., 1976). | | Solubility in water | Soluble in acetic acid, ether, ligroin (Weast, 1986), and very soluble in many chlorinated solvents
including chloroform, carbon tetrachloride, etc. | | Purification Methods | Crystallise it from EtOH. [Beilstein 5 H 204, 5 II 156, 5 III 550, 5 IV 667.] |
| | 1,2,3,4-Tetrachlorobenzene Preparation Products And Raw materials |
| Raw materials | 2,3,4-TRICHLOROANILINE-->Tetrachlorophthalic anhydride-->1,2,3-Trichlorobenzene | | Preparation Products | 1,2,3,5-Tetrachlorobenzene-->2,3,6-TRICHLOROPHENOL-->2,3,6-TRICHLOROANISOLE |
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