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Chloranil

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(Redirected from P-chloranil)
Chloranil
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.887 Edit this at Wikidata
EC Number
  • 204-274-4
KEGG
PubChem CID
RTECS number
  • DK6825000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11Key: UGNWTBMOAKPKBL-UHFFFAOYSA-N
  • InChI=1/C6Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11Key: UGNWTBMOAKPKBL-UHFFFAOYAV
SMILES
  • ClC=1C(=O)C(\Cl)=C(\Cl)C(=O)C=1Cl
Properties
Chemical formula C6Cl4O2
Molar mass 245.86 g·mol
Appearance Yellow solid
Melting point 295 to 296 °C (563 to 565 °F; 568 to 569 K)
Magnetic susceptibility (χ) -112.6·10 cm/mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS09: Environmental hazard
Signal word Warning
Hazard statements H315, H319, H410
Precautionary statements P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 that functions as a mild oxidant.

Synthesis and use as reagent

Chloranil is produced by chlorination of phenol to give hexachlorocyclohexa-2,5-dien-1-one ("hexachlorophenol"). Hydrolysis of the dichloromethylene group in this dienone gives chloranil:

C6H5OH + 6 Cl2 → C6Cl6O + 6 HCl
C6Cl6O + H2O → C6Cl4O2 + 2 HCl

Chloroanil serves as a hydrogen acceptor. It is more electrophilic than quinone itself. It is used for the aromatization reactions, such as the conversion of cyclohexadienes to the benzene derivatives.

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.

Commercial applications

It is a precursor to many dyes, such as pigment violet 23 and diaziquone (AZQ), a cancer chemotherapeutic agent.

See also

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. François Muller and Liliane Caillard "Chlorophenols" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2011. doi:10.1002/14356007.a07_001.pub2
  4. 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)
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