Tetrachlorobenzene

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Identifiers, Properties ...
Tetrachlorobenzene
1,2,3,4-Tetrachlorobenzene
1,2,3,5-Tetrachlorobenzene
1,2,4,5-Tetrachlorobenzene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.032.390 Edit this at Wikidata
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 Â°C [77 Â°F], 100 kPa).
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Properties

More information isomer, m.p. (°C) ...
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
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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 in the production of the herbicide 2,4,5-trichlorophenoxyacetic acid. This method has been discontinued because it produced highly toxic 2,3,7,8-tetrachlorodibenzo-p-dioxin as a waste product.[1][3][4]

See also

References

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