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1,2-Benzoquinone

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1,2-Benzoquinone
Names
IUPAC name cyclohexa-3,5-diene-1,2-dione
Other names 1,2-benzoquinone, o-benzoquinone, o-quinone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.243.463 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4HKey: WOAHJDHKFWSLKE-UHFFFAOYSA-N
  • InChI=1/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4HKey: WOAHJDHKFWSLKE-UHFFFAOYAR
SMILES
  • O=C1/C=C\C=C/C1=O
  • C1=CC(=O)C(=O)C=C1
Properties
Chemical 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
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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 or by ortho oxidation of a phenol. It is a precursor to melanin. 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 cathecol) as the final product.

See also

References

  1. ^ Magdziak, D., Rodriguez, A. A.; Van De Water, R. W.; Pettus, T. R. R. (2002). "Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX)". Org. Lett. 4 (2): 285–288. doi:10.1021/ol017068j. PMC 1557836. PMID 11796071.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. ^ Chanda Parulekar and Suneela Mavinkurve (2006), Formation of ortho-benzoquinone from sodium benzoate by Pseudomonas mendocina P2d. Indian Journal of Experimental Biology, volume 44, pages 157--162. Online version accessed on 2010-02-04.
  3. Enzymatic Browning in Fruits, Vegetables and Seafoods Section 2.3.2
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