1,2-Benzoquinone
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| Names | |||
|---|---|---|---|
| IUPAC name
cyclohexa-3,5-diene-1,2-dione | |||
| Other names
1,2-benzoquinone, o-benzoquinone, o-quinone | |||
| Identifiers | |||
583-63-1  | |||
| ChEBI | CHEBI:17253  | ||
| ChemSpider | 10941 | ||
| Jmol interactive 3D | Image Image | ||
| KEGG | C02351 | ||
| PubChem | 11421 | ||
| UNII | SVD1LJ47R7 | ||
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| Properties | |||
| C6H4O2 | |||
| Molar mass | 108.0964 g/mol | ||
| Density | 1.256 g/cm3 | ||
| Boiling point | 213.3 °C (415.9 °F; 486.4 K) at 760 mmHg | ||
| Hazards | |||
| Flash point | 76.4 °C (169.5 °F; 349.5 K) | ||
| Related compounds | |||
| Related compounds |
1,4-benzoquinone quinone | ||
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
| verify (what is ?) | |||
| Infobox references | |||
1,2-Benzoquinone, also called ortho-benzoquinone or cyclohexa-3,5-diene-1,2-dione, is a ketone, with formula | C=6 | H=4 | O=2 . 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 metabolises 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
- 1 2 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.
- 1 2 Chanda Parulekar and Suneela Mavinkurve (2006), Formation of ortho-benzoquinone from sodium benzoate by Pseudomonas mendocina | P=2 d. 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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