Tetrachlorobenzene

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]

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
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
SMILES 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

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 pesticides,^[3] specifically 2,4,5-trichlorophenol and 2,4,5-trichlorophenoxyacetic acid.^[4] This method has been discontinued because it also produced 2,3,7,8-tetrachlorodibenzo-p-dioxin.^[1]

See also

• Tetrabromobenzene
• Tetraiodobenzene