P-chloranil

Chloranil

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
CAS Number	118-75-2 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:36703 Y
ChEMBL	ChEMBL192627 Y
ChemSpider	8068 Y
ECHA InfoCard	100.003.887
KEGG	C18933 N
PubChem	8371
UNII	01W5X7N5XV Y
InChI InChI=1S/C6Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11 Y Key: UGNWTBMOAKPKBL-UHFFFAOYSA-N Y InChI=1/C6Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11 Key: UGNWTBMOAKPKBL-UHFFFAOYAV
SMILES ClC=1C(=O)C(\Cl)=C(\Cl)C(=O)C=1Cl
Properties
Chemical formula	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)
Magnetic susceptibility (χ)	-112.6·10−6 cm3/mol
Hazards
R-phrases	R36/38 R50/53
S-phrases	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 YN ?)
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.