Chloranil

Chloranil^[1]

Names
IUPAC name 2,3,5,6-Tetrachlorocyclohexa-2,5-diene-1,4-dione
Other names Tetrachloro-p-benzoquinone
Identifiers
CAS Registry Number	118-75-2 Y
ChEBI	CHEBI:36703 Y
ChEMBL	ChEMBL192627 Y
ChemSpider	8068 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
Jmol-3D images	Image
KEGG	C18933 N
PubChem	8371
SMILES ClC=1C(=O)C(\Cl)=C(\Cl)C(=O)C=1Cl
UNII	01W5X7N5XV Y
Properties
Chemical formula	C6Cl4O2
Molar mass	245.88 g/mol
Appearance	yellow solid
Melting point	295 to 296 °C (563 to 565 °F; 568 to 569 K)
Hazards
R-phrases	R36/38 R50/53
S-phrases	S37 S60 S61
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
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^[2] that functions as a mild oxidant.

Reagent

Chloroanil, more so than benzil, serves as a hydrogen acceptor. It is used for the aromatization reactions, such as the conversion of cyclohexadienes to the benzene derivatives.^[3]

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 p-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.

See also

• Chloranilic acid
• Chloranil in the Pesticide Properties DataBase (PPDB)
• Used as starting material to make diaziquone (AZQ), a cancer chemotherapeutic agent.

References