Structure via PubChem · Public domain (PubChem)
chloranil
Sign in to saveAlso known as 2,3,5,6-Tetrachlor-1,4-benzochinon, tetrachlorobenzoquinone, tetrachloro-p-benzoquinone, tetrachloro-1,4-benzoquinone, tetrachloroparabenzoquinone, 2,3,5,6-tetrachloro-2,5-cyclohexadiene-1,4-dione, alpha-chloranil, 2,3,5,6-tetrachloro-1,4-benzoquinone
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.
Chemical data
- Formula
- C6Cl4O2
- Molecular weight
- 245.9 g/mol
- IUPAC name
- 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione
- SMILES
- C1(=C(C(=O)C(=C(C1=O)Cl)Cl)Cl)Cl
- InChIKey
- UGNWTBMOAKPKBL-UHFFFAOYSA-N
- XLogP
- 3.4
- Polar surface area
- 34.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
705 papers- Lewis Acidity of the SbCl(3)/o-chloranil System.Angewandte Chemie (International ed. in English) · 2025
- Dissociative electron attachment to p-fluoranil and p-chloranil.The Journal of chemical physics · 2022
- The metabolic activation of pentachlorophenol to chloranil as a potent inhibitor of human and rat placental 3β-hydroxysteroid dehydrogenases.Toxicology letters · 2024
- Evolution of ferroelectricity in tetrathiafulvalene-p-chloranil as a function of pressure and temperature.The Journal of chemical physics · 2014
- Chloranil-photosensitized monomerization of dimethylthymine cyclobutane dimers and effect of magnesium perchlorate.Photochemistry and photobiology · 1990
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 243.86523996
Show 3 more facts
- canonical SMILES
- C1(=C(C(=O)C(=C(C1=O)Cl)Cl)Cl)Cl
- chemical formula
- C₆Cl₄O₂
- Commons category
- Chloranil
via Wikidata · CC0
~1 min read
Encyclopedic overview
5 sectionsContents
- Synthesis and use as reagent
- Commercial applications
- See also
- References
- External links
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
Excerpted from Wikipedia’s “chloranil” article, available under the CC BY-SA 4.0 licence.