| | 1,2,3,5-Tetrachlorobenzene Basic information |
| Product Name: | 1,2,3,5-Tetrachlorobenzene | | Synonyms: | 1,2,3,5-tcb;1,2,3,5-tetrachloro-benzen;1,2,4,6-tetrachlorobenzene;benzene,1,2,3,5-tetrachloro-;chlorinatedbenzenes,tri-,tetra-andpenta-;tetrachloro1,2,3,5-benzene;1,2,3,5-TETRACHLOROBENZENE OEKANAL, 250;1,2,3,5-TETRACHLOROBENZENE, 1X1ML MEOH 2 000UG/ML | | CAS: | 634-90-2 | | MF: | C6H2Cl4 | | MW: | 215.89 | | EINECS: | 211-217-7 | | Product Categories: | FINE Chemical & INTERMEDIATES;Benzene derivates;Single Component Standards for MISA AnalysesVolatiles/ Semivolatiles;Alpha Sort;Pesticides&Metabolites;Q-ZAlphabetic;Canada;International Standards;TA - TE;T-ZAlphabetic | | Mol File: | 634-90-2.mol |  |
| | 1,2,3,5-Tetrachlorobenzene Chemical Properties |
| Melting point | 54.5°C | | Boiling point | 246°C | | density | 1.5578 (estimate) | | vapor pressure | 0.07 at 25 °C (extrapolated, Mackay et al., 1982) | | refractive index | 1.5348 (estimate) | | Fp | 113 °C | | storage temp. | APPROX 4°C
| | solubility | Soluble in alcohol, benzene, ether, and ligroin (Weast, 1986) | | form | neat | | color | White to Almost white | | Water Solubility | 4.016mg/L(25 ºC) | | BRN | 1618864 | | Henry's Law Constant | 58.0 at 25 °C (gas stripping-GC, Shiu and Mackay, 1997) | | CAS DataBase Reference | 634-90-2(CAS DataBase Reference) | | NIST Chemistry Reference | Benzene, 1,2,3,5-tetrachloro-(634-90-2) | | EPA Substance Registry System | 1,2,3,5-Tetrachlorobenzene (634-90-2) |
| | 1,2,3,5-Tetrachlorobenzene Usage And Synthesis |
| Uses | 1,2,3,5-Tetrachlorobenzene is used in the synthesis of several organic compounds including that of polyarylated benzenes by multiple Suzuki-Miyaura reactions. It was used as part of study which investigated the antimicrobial activity of tetra substituted benzene derivatives which suggested antimicrobial activity tended to decrease with increasing size of halogen substituents. | | Definition | ChEBI: A tetrachlorobenzene carrying chloro groups at positions 1, 2, 3 and 5. | | General Description | White crystals or off-white solid. | | Air & Water Reactions | Insoluble in water. | | Reactivity Profile | Simple aromatic halogenated organic compounds, such as 1,2,3,5-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. 1,2,3,5-Tetrachlorobenzene may react with oxidizers. . | | Health Hazard | ACUTE/CHRONIC HAZARDS: 1,2,3,5-Tetrachlorobenzene may cause irritation on contact. | | Fire Hazard | 1,2,3,5-Tetrachlorobenzene is probably combustible. | | Environmental fate | Biological. A mixed culture of soil bacteria or a Pseudomonas sp. transformed 1,2,3,5-tetrachlorobenzene
to 2,3,4,6-tetrachlorophenol (Ballschiter and Scholz, 1980). The half-life of 1,2,3,5-
tetrachlorobenzene in an anaerobic enrichment culture was 1.8 d (Beurskens et al., 1993).
In an enrichment culture derived from a contaminated site in Bayou d’Inde, LA, 1,2,3,5-
tetrachlorobenzene underwent reductive dechlorination to 1,2,4- and 1,3,5-trichlorobenzene at
relative molar yields of 7 and 93%, respectively. The maximum dechlorination rate, based on the
recommended Michaelis-Menten model, was 94 nM/d (Pavlostathis and Prytula, 2000).
Photolytic. Irradiation (λ ≥285 nm) of 1,2,3,5-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 (5.3), 1,2,4-trichlorobenzene (4.9), 1,3,5-trichlorobenzene
(49.3), 1,3-dichlorobenzene (1.8), 2,3,4,4′,5,5′,6-heptachlorobiphenyl (1.41), 2,2′,3,4,4′,6,6′-
heptachlorobiphenyl (1.10), 2,2′,3,3′,4,5′,6-heptachlorobiphenyl (4.50), four hexachlorobiphenyls
(4.69), one pentachlorobiphenyl (0.64), trichloroacetophenone, 1-(trichlorophenyl)-2-propanone,
and (trichlorophenyl)acetonitrile (Choudhry and Hutzinger, 1984). Without acetone, the identified
photolysis products (% yield) included 1,2,3-trichlorobenzene (trace), 1,2,4-trichlorobenzene
(24.3), 1,3,5-trichlorobenzene (11.7), 1,3-dichlorobenzene (0.5), 1,4-dichlorobenzene (3.3),
pentachlorobenzene (1.43), 1,2,3,4-tetrachlorobenzene (5.99), two heptachlorobiphenyls (1.40),
two hexachlorobiphenyls (<0.01), and one pentachlorobiphenyl (0.75) (Choudhry and Hutzinger,
1984). | | Purification Methods | Crystallise it from EtOH. [Beilstein 5 II 157, 5 III 551, 5 IV 668.] |
| | 1,2,3,5-Tetrachlorobenzene Preparation Products And Raw materials |
| Raw materials | Cyclohexene, 1,2,3,4,5,6-hexachloro-, (3alpha,4beta,5beta,6alpha)--->Cyclohexene, 1,2,3,4,5,6-hexachloro--->1,2,3,4-Tetrachlorobenzene-->1-BROMO-2,4,6-TRICHLOROBENZENE-->2,4,6-Trichlorophenylhydrazine-->2,2',4,4',6,6'-HEXACHLOROBIPHENYL-->Methanol-->Dimethyl malonate-->2,4,6-Trichloroaniline-->1,3,5-Trichlorobenzene | | Preparation Products | 2,4,5-Trichlorophenol-->1,2,4,5-Tetrachlorobenzene |
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