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1,2-Benzoquinone

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1,2-Benzoquinone

1,2-Benzoquinone
Names
IUPAC name
cyclohexa-3,5-diene-1,2-dione
Other names
1,2-benzoquinone, o-benzoquinone, o-quinone
Identifiers
 N
ChEBI  YesY
ChemSpider  YesY
Jmol-3D images Image
Image
KEGG  YesY
PubChem
UNII  YesY
Properties
small=yes}}} }}} 0}}} 1=C|C} }}} 1=H|H} }}} 1=Ac|Ac} }}} 1=Ag|Ag} }}} 1=Al|Al} }}} 1=Am|Am} }}} 1=Ar|Ar} }}} 1=As|As} }}} 1=At|At} }}} 1=Au|Au} }}} 1=B|B} }}} 1=Ba|Ba} }}} 1=Be|Be} }}} 1=Bh|Bh} }}} 1=Bi|Bi} }}} 1=Bk|Bk} }}} 1=Br|Br} }}} 1=Ca|Ca} }}} 1=Cd|Cd} }}} 1=Ce|Ce} }}} 1=Cf|Cf} }}} 1=Cn|Cn} }}} 1=Cl|Cl} }}} 1=Cm|Cm} }}} 1=Co|Co} }}} 1=Cr|Cr} }}} 1=Cs|Cs} }}} 1=Cu|Cu} }}} 1=Db|Db} }}} 1=Ds|Ds} }}} 1=Dy|Dy} }}} 1=Er|Er} }}} 1=Es|Es} }}} 1=Eu|Eu} }}} 1=F|F} }}} 1=Fe|Fe} }}} 1=Fl|Fl} }}} 1=Fm|Fm} }}} 1=Fr|Fr} }}} 1=Ga|Ga} }}} 1=Gd|Gd} }}} 1=Ge|Ge} }}} 1=He|He} }}}}
Documentation

Density 1.256 g/cm3
Boiling point 213.3 °C (415.9 °F; 486.5 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).
 N  (: YesY/N?)

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 metabolises benzoic acid, yielding 1,2-benzoquinone (via catechol) as the final product.[2]

See also

References

  1. ^ a b
  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


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