1,2-Benzoquinone

1,2-Benzoquinone
IUPAC name cyclohexa-3,5-diene-1,2-dione
Other names 1,2-benzoquinone, o-benzoquinone, o-quinone
Identifiers
CAS number	583-63-1 N
PubChem	11421
ChemSpider	10941 Y
UNII	SVD1LJ47R7 Y
KEGG	C02351 Y
ChEBI	CHEBI:17253 Y
Jmol-3D images	Image 1 Image 2
SMILES O=C1/C=C\C=C/C1=O C1=CC(=O)C(=O)C=C1
InChI InChI=1S/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4H Y Key: WOAHJDHKFWSLKE-UHFFFAOYSA-N Y InChI=1/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4H Key: WOAHJDHKFWSLKE-UHFFFAOYAR
Properties
Molecular formula	C6H4O2
Molar mass	108.0964 g/mol
Density	1.256 g/cm3
Boiling point	213.3 °C @760 mmHg
Hazards
Flash point	76.4 °C; 169.5 °F; 349.5 K
Related compounds
Related compounds	1,4-benzoquinone quinone
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

1,2-Benzoquinone, also called ortho-benzoquinone or cyclohexa-3,5-diene-1,2-dione, is a ketone, with formula C₆H₄O₂. It is one of the two isomers of quinone, the other being 1,4-benzoquinone.

1,2-Benzoquinone is produced on oxidation of catechol exposed to air in aqueous solution^[1][2] or by ortho oxidation of a phenol.^[1] It is a precursor to melanin.^[3] It is a red substance soluble in water and insoluble in ethyl ether.

A strain of the bacterium Pseudomonas mendocina metabolyzes benzoic acid yielding 1,2-benzoquinone (via catechol) as the final product.^[2]

See also

• 1,4-Benzoquinone
• Tetrabromo-1,2-benzoquinone (o-bromanil)
• Tetrachloro-1,2-benzoquinone (o-chloranil)
• Tetrahydroxy-1,2-benzoquinone
• Hydroxybenzoquinone

References