Hexachlorocyclohexa-2,5-dien-1-one

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Hexachlorocyclohexa-2,5-dien-1-one
Structural formula of hexachlorocyclohexa-2,5-dien-1-one Hexachlorocyclohexa-2,5-dien-1-one.svg
Structural formula of hexachlorocyclohexa-2,5-dien-1-one
Hexachlorocyclohexa-2,5-dien-1-one-3D-balls.png
Names
Preferred IUPAC name
2,3,4,4,5,6-Hexachlorocyclohexa-2,5-dien-1-one
Other names
Hexachlorophenol
Identifiers
3D model (JSmol)
AbbreviationsHCP
ChemSpider
PubChem CID
RTECS number
  • SN1575000
  • 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)
Hazards [1]
GHS labelling:
GHS-pictogram-exclam.svg
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).

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. [2] The informal name is derived from its method of preparation which includes phenol as a reagent.

Contents

Preparation

HCP is normally produced by chlorination of phenol by chlorine in the presence of metal chloride catalyst, such as ferric chloride. 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]

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In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (−OH) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, C
6
H
5
OH
. Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule.

<span class="mw-page-title-main">Haloalkane</span> Group of chemical compounds derived from alkanes containing one or more halogens

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2,6-Dichlorophenol is a compound with formula C6H3Cl2OH. It is one of the six isomers of dichlorophenol. It is a colorless solid. Its pKa is 6.78, which is about 100x more acidic than 2-chlorophenol (8.52) and 1000x more acidic than phenol itself (9.95).

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ortho-Cresol (IUPAC name: 2-methylphenol, also known as 2-hydroxytoluene or ortho-Toluenol) is an organic compound with the formula CH3C6H4(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of p-cresol and m-cresol.

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Dimethylcarbamoyl chloride (DMCC) is a reagent for transferring a dimethylcarbamoyl group to alcoholic or phenolic hydroxyl groups forming dimethyl carbamates, usually having pharmacological or pesticidal activities. Because of its high toxicity and its carcinogenic properties shown in animal experiments and presumably also in humans, dimethylcarbamoyl chloride can only be used under stringent safety precautions.

4-Chlorophenol is an organic compound with the formula C6H4ClOH. It is one of three monochlorophenol isomers. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Its pKa is 9.14.

References

  1. "SAFETY DATA SHEET". ThermoFisher Scientific. 18 December 2020.
  2. S. Gali, C. Miravitlles and M. Font-Altaba "Hexachlorocyclohexa-2,5-dienone" Acta Crystallogr. 1975, volume B31, p. 2510-2512. doi : 10.1107/S0567740875007935.
  3. François Muller; Liliane Caillard (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2. ISBN   978-3527306732.

See also