O-benzoquinone

Also known as ortho-benzoquinone, cyclohexa-3,5-diene-1,2-dione, 3,5-cyclohexadiene-1,2-dione, o-quinone, 2-benzoquinone, 1,2-Benzoquinone, catechol quinone

1,2-Benzoquinone, also called '''ortho-benzoquinone''', is an organic compound with formula . It is one of the two isomers of quinone, the other being 1,4-benzoquinone. It is a red volatile solid that is soluble in water and diethyl ether. It is rarely encountered because of its instability, but it is of fundamental interest as the parent compound of many derivatives which are known.

Chemical data

Formula: C6H4O2
Molecular weight: 108.09 g/mol
IUPAC name: cyclohexa-3,5-diene-1,2-dione
SMILES: C1=CC(=O)C(=O)C=C1
InChIKey: WOAHJDHKFWSLKE-UHFFFAOYSA-N
XLogP: 0.4
Polar surface area: 34.1 Å²
H-bond donors: 0
H-bond acceptors: 2
Formal charge: 0

via PubChem

Wikidata facts

Subclass of: chemical compound
Has part: hydrogen
Mass: 108.021129

Show 5 more facts

chemical formula: C₆H₄O₂
canonical SMILES: C1=CC(=O)C(=O)C=C1
Commons category: 1,2-Benzoquinone
found in taxon: Salvia abrotanoides
melting point: 65

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Encyclopedic overview

5 sections

Contents

Structure
Preparation and reactions
Occurrence of ''ortho''-quinones
See also
References

1,2-Benzoquinone, also called '''ortho-benzoquinone', is an organic compound with formula . It is one of the two isomers of quinone, the other being 1,4-benzoquinone. It is a red volatile solid that is soluble in water and diethyl ether. It is rarely encountered because of its instability, but it is of fundamental interest as the parent compound of many derivatives which are known.

==Structure== The molecule has C symmetry. X-ray crystallography shows that the double bonds are localized, with alternatingly long and short C-C distances within the ring. The C=O distances of 1.21 Å are characteristic of ketones.

Excerpted from Wikipedia’s “O-benzoquinone” article, available under the CC BY-SA 4.0 licence.