Hexachlorobenzene

Hexachlorobenzene
Skeletal formula of hexachlorobenzene
Skeletal formula of hexachlorobenzene
Ball-and-stick model of hexachlorobenzene
Ball-and-stick model of hexachlorobenzene
Names
Preferred IUPAC name
Hexachlorobenzene
Other names
Perchlorobenzene; HCB; Julin's chloride of carbon
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.886 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9 checkY
    Key: CKAPSXZOOQJIBF-UHFFFAOYSA-N checkY
  • InChI=1/C6Cl6/c7-1-2(8)4(10)6(12)5(11)3(1)9
    Key: CKAPSXZOOQJIBF-UHFFFAOYAV
  • c1(Cl)c(Cl)c(Cl)c(Cl)c(Cl)c1Cl
Properties
C6Cl6
Molar mass 284.77 g·mol−1
Appearance White crystalline solid
Density 2.04 g/cm3
Melting point 228.83 °C (443.89 °F; 501.98 K)[1]
Boiling point 325 °C (617 °F; 598 K)[1]
insoluble
Solubility in other solvents slightly soluble in ethanol; soluble in diethyl ether and chloroform; very soluble in benzene[1]
log P 5.47[2]
−147.0·10−6 cm3/mol[3]
Thermochemistry[5]
201.2 J·mol−1·K−1
260.2 J·mol−1·K−1
−127.6 kJ·mol−1
Enthalpy of fusion (ΔfH⦵fus)
 25.2 kJ·mol−1[4]
Related compounds
Related compounds
 Benzene
Hexafluorobenzene
Hexabromobenzene
Hexaiodobenzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Hexachlorobenzene, or perchlorobenzene, is an aryl chloride and a six-substituted chlorobenzene with the molecular formula C6Cl6. It is a fungicide formerly used as a seed treatment, especially on wheat to control the fungal disease bunt. It has been banned globally under the Stockholm Convention on Persistent Organic Pollutants.[6]

  1. ^ a b c Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. p. 3-276. ISBN 978-1-4200-9084-0.
  2. ^ Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. p. 16-42. ISBN 978-1-4200-9084-0.
  3. ^ Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. p. 3-674. ISBN 978-1-4200-9084-0.
  4. ^ Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. p. 6-137. ISBN 978-1-4200-9084-0.
  5. ^ Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. p. 5-30. ISBN 978-1-4200-9084-0.
  6. ^ Stockholm Convention on Persistent Organic Pollutants website Archived 2014-04-16 at the Wayback Machine