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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.887 Edit this at Wikidata
EC Number
  • 204-274-4
KEGG
RTECS number
  • DK6825000
UNII
UN number 3077
  • InChI=1S/C6Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11 checkY
    Key: UGNWTBMOAKPKBL-UHFFFAOYSA-N checkY
  • InChI=1/C6Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11
    Key: UGNWTBMOAKPKBL-UHFFFAOYAV
  • ClC=1C(=O)C(\Cl)=C(\Cl)C(=O)C=1Cl
Properties[3]
C6Cl4O2
Molar mass 245.86 g·mol−1
Appearance Yellow solid
Density 1.97 g⋅cm−3[1]
Melting point 298.3 °C (568.9 °F; 571.5 K)
Boiling point Sublimes
0.25 g/kg (20 °C (68 °F))
Solubility in Ethanol Slightly soluble
Solubility in Chloroform Slightly soluble
Solubility in Diethyl ether Soluble
log P 2.3 (20 °C (68 °F))[2]
Vapor pressure 1 hPa (71 °C (160 °F))[1]
−112.6×10−6 cm3/mol[citation needed]
Structure[4]
Monoclinic
P21/c (C5
2h)
2/m
a = 8.86 Å, b = 5.83 Å, c = 8.76 Å
α = 90°, β = 72.6°, γ = 90°
2
Hazards[2]
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation markGHS09: Environmental hazard
Danger
H315, H317, H318, H410
P261, P264, P272, P273, P280, P302+P352, P305+P351+P338+P310, P333+P313, P362, P391, P501
NFPA 704 (fire diamond)
[1]
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Flash point >100 °C (212 °F)[1]
>400 °C (752 °F)
Lethal dose or concentration (LD, LC):
4000 mg/kg (rat, oral)
24.85 mg/m3 (rat, inhalation, 4h)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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[5] 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:[6]

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.[7]

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.[citation needed]

Commercial applications

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

See also

References

  1. ^ a b c d "SDS - Tetrachloro-p-benzoquinone". www.fishersci.com. Revision 6. ThermoFisher Scientific. 19 December 2025. p. 3. Retrieved 5 June 2026.
  2. ^ a b Sigma-Aldrich Co., Tetrachloro-1,4-benzoquinone.
  3. ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). Boca Raton, Florida: CRC Press. pp. 3–496. ISBN 9781498754293.
  4. ^ Ueda, Ikuhiko (June 1961). "The Crystal Structure of Chloranil and Bromanil". Journal of the Physical Society of Japan. 16 (6): 1185–1194. doi:10.1143/JPSJ.16.1185.
  5. ^ Lü, Jian-Ming; Rosokha, Sergiy V.; Neretin, Ivan S.; Kochi, Jay K. (1 December 2006). "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. 128 (51): 16708–16719. doi:10.1021/ja066471o.
  6. ^ Muller, François; Caillard, Liliane (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2. ISBN 978-3-527-30673-2.
  7. ^ Buckle, Derek R. (15 April 2001). "Chloranil". Encyclopedia of Reagents for Organic Synthesis. John Wiley. doi:10.1002/047084289X.rc057.
  • Chloranil in the Pesticide Properties DataBase (PPDB)

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