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Chloranil

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
ChemSpider
ECHA InfoCard 100.003.887
KEGG
PubChem CID
UNII
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
R-phrases (outdated) R36/38 R50/53
S-phrases (outdated) S37 S60 S61
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

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.

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:

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.

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


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