Chloranil

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Chloranil[1]
2,3,5,6-tetrachloro-parabenzoquinone.svg
Names
IUPAC name
2,3,5,6-Tetrachlorocyclohexa-2,5-diene-1,4-dione
Other names
Tetrachloro-p-benzoquinone
Identifiers
118-75-2 YesY
ChEBI CHEBI:36703 YesY
ChEMBL ChEMBL192627 YesY
ChemSpider 8068 YesY
Jmol-3D images Image
KEGG C18933 N
PubChem 8371
UNII 01W5X7N5XV YesY
Properties
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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/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[edit]

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[edit]

References[edit]

  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