Hexachlorocyclohexa-2,5-dien-1-one

Hexachlorocyclohexa-2,5-dien-1-one
Structural formula of hexachlorocyclohexa-2,5-dien-1-one
Structural formula of hexachlorocyclohexa-2,5-dien-1-one
Hexachlorophenol molecule
Names
Preferred IUPAC name
2,3,4,4,5,6-Hexachlorocyclohexa-2,5-dien-1-one
Other names
Hexachlorophenol
Identifiers
3D model (JSmol)
Abbreviations HCP
ChemSpider
RTECS number
  • SN1575000
UNII
  • InChI=1S/C6Cl6O/c7-1-3(13)2(8)5(10)6(11,12)4(1)9
    Key: SLKWROUNLHVIIQ-UHFFFAOYSA-N
  • ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C(Cl)C1=O
  • O=C1C(=C(Cl)C(Cl)(Cl)C(=C1Cl)Cl)Cl
Properties
C6Cl6O
Molar mass 300.77 g·mol−1
Melting point 113 °C (235 °F; 386 K)
Structure[1]
Tetragonal
I41/a
4/m
a = 21.796 Å, c = 8.568 Å
4070.36 Å3
16
Hazards[2]
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P280, P302+P352, P305+P351+P338
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Hexachlorocyclohexa-2,5-dien-1-one, sometimes informally called hexachlorophenol (HCP), is an organochlorine compound. It can be prepared from phenol. Despite the informal name, the compound is not a phenol but is a ketone.[1] The informal name may be derived from its method of preparation, which includes phenol as a reagent. It is a white solid with herbicidal properties.

Preparation and reactions

HCP is normally produced by chlorination of phenol by chlorine in aqueous acetic acid.[3]

It can also be produced by alkaline hydrolysis of polychlorinated benzenes at high temperature and pressure, by conversion of diazonium salts of chlorinated anilines, or by chlorination of phenolsulfonic acids and benzenesulfonic acids followed by removal of the sulfonic acid group.

The hydrolysis of HCP gives chloranil.[3]

References

  1. 1 2 Gali, S.; Miravitlles, C.; Font-Altaba, M. (1 October 1975). "Hexachlorocyclohexa-2,5-dienone". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 31 (10): 2510–2512. doi:10.1107/S0567740875007935.
  2. ↑ "SAFETY DATA SHEET". ThermoFisher Scientific. 18 December 2020.
  3. 1 2 François Muller; Liliane Caillard (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2. ISBN 978-3-527-30673-2.

See also

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