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
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
Related compounds
Related compounds	1,4-benzoquinone quinone
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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 cathecol) 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. ^ ^{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. 
2. ^ ^{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.
3. ^ Enzymatic Browning in Fruits, Vegetables and Seafoods Section 2.3.2

This article about a ketone is a stub. You can help Wikipedia by expanding it.v · Categories: Benzoquinones Ketone stubs Wikimedia Foundation. 2010. Игры ⚽ Поможем сделать НИР Channel 3 (Iran) Uppland Runic Inscription 705 Look at other dictionaries: benzoquinone — ● benzoquinone nom féminin Quinone C6H4O2, dérivée du benzène, dont il existe 2 isomères, l orthobenzoquinone et la parabenzoquinone, prototype des quinones, qui s obtient par l oxydation énergique de nombreux dérivés du benzène et dont la… …   Encyclopédie Universelle Benzoquinone — Cette page d’homonymie répertorie les différents sujets et articles partageant un même nom. Benzoquinone peut faire allusion à deux isomères : 1,2 Benzoquinone 1,4 Benzoquinone Catégorie : Homonymie …   Wikipédia en Français benzoquinone — ben·zo·qui·none .ben zō kwin ōn, kwin . n QUINONE (1) * * * ben·zo·qui·none (ben″zo kwinґōn) 1. a substituted benzene ring containing two carbonyl groups, usually in the para (1,4) position. p Benzoquinone is used in the manufacture of …   Medical dictionary benzoquinone — noun Etymology: International Scientific Vocabulary Date: 1903 quinone 1 …   New Collegiate Dictionary benzoquinone —       simplest member of the quinone family of organic compounds; see quinone. * * * …   Universalium benzoquinone — noun Either of the two isomeric forms of the simplest quinone, CHO, or any of their derivatives. Syn: cyclohexadienedione …   Wiktionary Benzoquinone — Бензохинон, хинон C6H4O2 …   Краткий толковый словарь по полиграфии benzoquinone — [ˌbɛnzə(ʊ) kwɪnəʊn] noun Chemistry a yellow crystalline compound related to benzene but having two hydrogen atoms replaced by oxygen …   English new terms dictionary benzoquinone — ben·zo·quinone …   English syllables benzoquinone — /ˌbɛnzoʊkwəˈnoʊn/ (say .benzohkwuh nohn) noun → quinone (def. 1) …   benzoquinone — noun any of a class of aromatic yellow compounds including several that are biologically important as coenzymes or acceptors or vitamins; used in making dyes • Syn: ↑quinone • Hypernyms: ↑compound, ↑chemical compound • Hyponyms: ↑ubiquinone, ↑ …   Useful english dictionary 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”