Tetrachlorobenzene

Tetrachlorobenzene is any of three isomeric chlorinated derivatives with the molecular formula C6H2Cl4. They differ by the positions of the chlorine atoms around the ring. Tetrachlorobenzenes are colorless crystalline compounds.[1]

Tetrachlorobenzene

1,2,3,4-Tetrachlorobenzene

1,2,3,5-Tetrachlorobenzene

1,2,45-Tetrachlorobenzene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.032.390
EC Number
  • 1,2,4,5: 202-466-2
  • 1,2,3,5: 211-217-7
  • 1,2,3,4: 211-214-0
KEGG
RTECS number
  • 1,2,4,5: DB9450000
UNII
  • 1,2,4,5: InChI=1S/C6H2Cl4/c7-3-1-4(8)6(10)2-5(3)9/h1-2H
    Key: JHBKHLUZVFWLAG-UHFFFAOYSA-N
  • 1,2,3,5: InChI=1S/C6H2Cl4/c7-3-1-4(8)6(10)5(9)2-3/h1-2H
    Key: QZYNWJQFTJXIRN-UHFFFAOYSA-N
  • 1,2,3,4: InChI=1S/C6H2Cl4/c7-3-1-2-4(8)6(10)5(3)9/h1-2H
    Key: GBDZXPJXOMHESU-UHFFFAOYSA-N
  • 1,2,4,5: C1=C(C(=CC(=C1Cl)Cl)Cl)Cl
  • 1,2,3,5: C1=C(C=C(C(=C1Cl)Cl)Cl)Cl
  • 1,2,3,4: C1=CC(=C(C(=C1Cl)Cl)Cl)Cl
Properties
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).
Infobox references

Properties
Selected Physical Properties of Individual Isomers
isomerm.p. (°C)b.p. (°C)m.p. (g/cm3 @100 °C)
1,2,3,4472541.539
1,2,3,551.52461.523
1,2,4,51412451.454

Synthesis

1,2,4,5-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

1,2,4,5-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

References
  1. 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.
  2. "US4205014A Process for 1,2,4,5-tetrachlorobenzene". Espacenet. Retrieved 22 June 2023.
  3. NTP Toxicity Study Reports. National Toxicology Program. 1991. p. 11. Retrieved 22 June 2023.
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