1,2-Benzoquinone
| 1,2-Benzoquinone | |
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cyclohexa-3,5-diene-1,2-dione |
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Other names
1,2-benzoquinone, o-benzoquinone, o-quinone |
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| Identifiers | |
| CAS number | 583-63-1 |
| PubChem | 11421 |
| ChemSpider | 10941  |
| UNII | SVD1LJ47R7 |
| KEGG | C02351 |
| ChEBI | CHEBI:17253 |
| Jmol-3D images | Image 1 Image 2 |
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| 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 |
| Related compounds | |
| Related compounds | 1,4-benzoquinone quinone |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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 cathecol) as the final product.[2]
[edit] See also
- 1,4-Benzoquinone
- Tetrabromo-1,2-benzoquinone (o-bromanil)
- Tetrachloro-1,2-benzoquinone (o-chloranil)
- Tetrahydroxy-1,2-benzoquinone
- Hydroxybenzoquinone
[edit] References
- ^ a b 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1557836.
- ^ a b 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.
- ^ Enzymatic Browning in Fruits, Vegetables and Seafoods Section 2.3.2
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