Tetrachlorobenzene

Tetrachlorobenzene

1,2,3,4-Tetrachlorobenzene

1,2,3,5-Tetrachlorobenzene

1,2,4,5-Tetrachlorobenzene
Identifiers
CAS Number
  • mix: 12408-10-5
  • 1,2,4,5: 95-94-3
  • 1,2,3,5: 634-90-2
  • 1,2,3,4: 634-66-2
3D model (JSmol)
  • 1,2,4,5: Interactive image
  • 1,2,3,5: Interactive image
  • 1,2,3,4: Interactive image
ChEBI
  • 1,2,4,5: CHEBI:36697
  • 1,2,3,5: CHEBI:36696
  • 1,2,3,4: CHEBI:18855
ChEMBL
  • 1,2,4,5: ChEMBL45428
  • 1,2,3,5: ChEMBL44011
  • 1,2,3,4: ChEMBL46422
ChemSpider
  • 1,2,4,5: 21106163
  • 1,2,3,5: 21106571
  • 1,2,3,4: 21106540
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
  • 1,2,3,4: C18236
PubChem CID
  • 1,2,4,5: 7270
  • 1,2,3,5: 12468
  • 1,2,3,4: 12463
RTECS number
  • 1,2,4,5: DB9450000
UNII
  • 1,2,4,5: 5N27529KGH
  • 1,2,3,5: I27N186CIN
  • 1,2,3,4: MH0UY3V1KE
CompTox Dashboard (EPA)
  • 1,2,4,5: DTXSID7024320
  • 1,2,3,5: DTXSID1026089
  • 1,2,3,4: DTXSID6026088
InChI
  • 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
Chemical formula
 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
Chemical compound

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]

Properties

Selected Physical Properties of Individual Isomers
isomer m.p. (°C) b.p. (°C) m.p. (g/cm3 @100 °C)
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

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. ^ 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.
  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.