1,2-Benzoquinone

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1,2-Benzoquinone

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Template:Longitem	Template:Chembox Elements/molecular formula
Molar mass	Template:Chem molar mass
Appearance	Red volatile solid
Density	1.424 g/cm3
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Template:Longitem	1,4-benzoquinone quinone

1,2-Benzoquinone, also called ortho-benzoquinone, is an organic compound with formula Template:Chem2. It is one of the two isomers of quinone, the other being 1,4-benzoquinone. It is a red volatile solid that is soluble in water and diethyl ether. It is rarely encountered because of its instability, but it is of fundamental interest as the parent compound of many derivatives which are known.

Structure

The molecule has C_2v symmetry. X-ray crystallography shows that the double bonds are localized, with alternatingly long and short C-C distances within the ring. The C=O distances of 1.21 Å are characteristic of ketones.

Preparation and reactions

1,2-Benzoquinone is produced on oxidation of catechol exposed to air in aqueous solution or by ortho oxidation of a phenol.

A strain of the bacterium Pseudomonas mendocina metabolises benzoic acid, yielding 1,2-benzoquinone via catechol.

Ortho-quinones are widely used in organic synthesis.

Occurrence of ortho-quinones

File:Lysine Tyrosylquinone Mediated Oxn of Lysine.svg

The oxidation of lysyl side chains is effected in nature by the action of an orthoquinone called lysyl tyrosylquinone.

4,5-Dimethyl-1,2-benzoquinone, also a red solid, is a well behaved synthetic ortho-quinone.

The biological pigment melanin is rich in ortho-quinones.

Finally, the enzyme cofactors tryptophan tryptophylquinone (TTQ), cysteine tryptophylquinone (CTQ), lysine tyrosylquinone (LTQ) and pyrroloquinoline quinone (PQQ) contain the ortho-quinone moiety in their chemical structure.

See also

• 1,4-Benzoquinone