Chloranil

Chloranil^[1]

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
ChEBI	CHEBI:36703
ChEMBL	ChEMBL192627
ChemSpider	8068
Jmol interactive 3D	Image
KEGG	C18933
PubChem	8371
UNII	01W5X7N5XV
InChI InChI=1S/C6Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11 Key: UGNWTBMOAKPKBL-UHFFFAOYSA-N 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)
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).
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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 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.

Chloranil is used as starting material to make diaziquone (AZQ), a cancer chemotherapeutic agent.

See also

• Chloranilic acid
• 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)

References

1. Chloranil at Sigma-Aldrich
2. J.-M. Lü, S. V. Rosokha, I. S. Neretin and J. K. Kochi, "Quinones as Electron Acceptors. X-Ray Structures, Spectral (EPR, UV-vis) Characteristics and Electron-Transfer Reactivities of Their Reduced Anion Radicals as Separated vs Contact Ion Pairs" Journal of the American Chemical Society 2006 128, 16708-16719.doi:10.1021/ja066471o
3. Derek R. Buckle "Chloranil" in Encyclopedia of Reagents for Organic Synthesis, 2001, John Wiley. doi:10.1002/047084289X.rc057

External links

• Chloranil in the Pesticide Properties DataBase (PPDB)