Tetrachlorobenzene is any of three isomeric chlorobenzenes with the molecular formula C6H2Cl4. They differ by the positions of the chlorine atoms around the ring. Tetrachlorobenzenes are colorless crystalline compounds.[1]
 1,2,3,4-Tetrachlorobenzene
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 1,2,3,5-Tetrachlorobenzene
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 1,2,4,5-Tetrachlorobenzene
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| ECHA InfoCard | 100.032.390 |
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| C6H2Cl4 | |
| Molar mass | 215.88 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Properties
edit| isomer | m.p. (°C) | b.p. (°C) | m.p. (g/cm3 @100 °C) |
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| 1,2,3,4 | 47 | 254 | 1.539 |
| 1,2,3,5 | 51.5 | 246 | 1.523 |
| 1,2,4,5 | 141 | 245 | 1.454 |
Synthesis
edit1,2,4,5-Tetrachlorobenzene can be produced by electrophilic halogenation of benzenes and some chlorobenzenes.[2] 1,2,3,4-Tetrachlorobenzene can only be produced by chlorination of 1,3,5-trichlorobenzene.
Uses
edit1,2,4,5-tetrachlorobenzene once was used as intermediates in the production of pesicides,[3] specifically trichlorophenols. This method has been discontinued because it also produced 2,3,7,8-tetrachlorodibenzo-p-dioxin.[1]
See also
editReferences
edit- ^ a b Beck, Uwe; Löser, Eckhard (2011). "Chlorinated Benzenes and Other Nucleus-Chlorinated Aromatic Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.o06_o03. ISBN 9783527303854.
- ^ "US4205014A Process for 1,2,4,5-tetrachlorobenzene". Espacenet. Retrieved 22 June 2023.
- ^ NTP Toxicity Study Reports. National Toxicology Program. 1991. p. 11. Retrieved 22 June 2023.