Chloranil

Chloranil^[1]
Names
	IUPAC name 2,3,5,6-Tetrachlorocyclohexa-2,5-diene-1,4-dione
	Other names Tetrachloro-p-benzoquinone
Identifiers
CAS Number	118-75-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:36703 ;
ChEMBL	ChEMBL192627 ;
ChemSpider	8068 ;
ECHA InfoCard	100.003.887
KEGG	C18933 ;
PubChem CID	8371;
UNII	01W5X7N5XV ;
CompTox Dashboard (EPA)	DTXSID2020266 ;
	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	245.88 g/mol
Appearance	yellow solid
Melting point	295–296 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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, moreso 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.

References

^ Chloranil at Sigma-Aldrich
^ 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
^ Derek R. Buckle "Chloranil" in Encyclopedia of Reagents for Organic Synthesis 2001, John Wiley. doi:10.1002/047084289X.rc057

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[1] Chloranil at Sigma-Aldrich

[Kochi-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

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Reagent

See also

References