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
p-Chloranil; Tetrachloro-1,4-benzoquinone; Tetrachloro-p-benzoquinone
Identifiers
118-75-2 YesY
ChEBI CHEBI:36703 YesY
ChEMBL ChEMBL192627 YesY
ChemSpider 8068 YesY
Jmol interactive 3D Image
KEGG C18933 N
PubChem 8371
UNII 01W5X7N5XV YesY
Properties
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).
N verify (what is YesYN ?)
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 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[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

External links[edit]

  • Chloranil in the Pesticide Properties DataBase (PPDB)