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Fungicides
Chloranil
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Chloranil

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Chloranil
Chloranil structure.png
Names
IUPAC name
2,3,5,6-Tetrachlorocyclohexa-2,5-diene-1,4-dione
Other names
p-Chloranil; Tetrachloro-1,4-benzoquinone; Tetrachloro-p-benzoquinone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.887
EC Number
  • 204-274-4
KEGG
PubChem CID
RTECS number
  • DK6825000
UNII
  • InChI=1S/C6Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11 checkY
    Key: UGNWTBMOAKPKBL-UHFFFAOYSA-N checkY
  • InChI=1/C6Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11
    Key: UGNWTBMOAKPKBL-UHFFFAOYAV
  • ClC=1C(=O)C(\Cl)=C(\Cl)C(=O)C=1Cl
Properties
C6Cl4O2
Molar mass 245.86 g·mol−1
Appearance Yellow solid
Melting point 295 to 296 °C (563 to 565 °F; 568 to 569 K)
-112.6·10−6 cm3/mol
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H315, H319, H410
P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Chloranil is a quinone with the molecular formula C6Cl4O2. Also known as tetrachloro-1,4-benzoquinone, it is a yellow solid. Like the parent benzoquinone, chloranil is a planar molecule that functions as a mild oxidant.

Synthesis and use as reagent

Chloranil is produced by chlorination of phenol to give hexachlorocyclohexa-2,5-dien-1-one ("hexachlorophenol"). Hydrolysis of the dichloromethylene group in this dienone gives chloranil:

C6H5OH + 6 Cl2 → C6Cl6O + 6 HCl
C6Cl6O + H2O → C6Cl4O2 + 2 HCl

Chloroanil serves as a hydrogen acceptor. It is more electrophilic than quinone itself. It is used for the aromatization reactions, such as the conversion of cyclohexadienes to the benzene derivatives.

Chloranil is used to test for free secondary amines. This test is useful for checking for the presence of proline derivatives. It is also a good test for the successful deprotection of a secondary amine. Secondary amines react with chloranil to give a brown/red/orange derivative, the colour depending on the amine. In these reactions, the amine displaces chloride from the ring of the quinone.

Commercial applications

It is a precursor to many dyes, such as pigment violet 23 and diaziquone (AZQ), a cancer chemotherapeutic agent.

See also

External links

  • Chloranil in the Pesticide Properties DataBase (PPDB)

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