1,2-Benzoquinone Explained

1,2-Benzoquinone, also called ortho-benzoquinone, is an organic compound with formula . 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 ethyl 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.^{[1] [2]}

Structure

The molecule has C 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.^[3]

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.^[4]

A strain of the bacterium Pseudomonas mendocina metabolises benzoic acid, yielding 1,2-benzoquinone via catechol.^[5]

Ortho-quinones are widely used in organic synthesis.^[6]

Occurrence of ortho-quinones

4,5-Dimethyl-1,2-benzoquinone, also a red solid, is a well behaved synthetic ortho-quinone.^[7]

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.^[8]

See also

• 1,4-Benzoquinone

Notes and References

1. Book: 10.1002/9780470771297 . Quinonoid Compounds: Vol. 1 (1974) . 1974 . 9780470771297 . Patai . Saul. PATAI'S Chemistry of Functional Groups.
2. Book: 10.1002/9780470771303 . Quinonoid Compounds: Vol. 2 (1974) . 1974 . 9780470771303 . Patai . Saul. PATAI'S Chemistry of Functional Groups.
3. 10.1039/P29730000476. Crystal and molecular structure of o-benzoquinone. Journal of the Chemical Society, Perkin Transactions 2. 4. 476. 1973. MacDonald. Alistair L.. Trotter. James.
4. Magdziak, D. . Rodriguez, A. A. . Van De Water, R. W. . Pettus, T. R. R. . Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX) . . 4 . 2 . 285–288 . 2002 . 10.1021/ol017068j . 1557836 . 11796071.
5. Chanda Parulekar and Suneela Mavinkurve . 2006 . Formation of ortho-benzoquinone from sodium benzoate by Pseudomonas mendocina P₂d . Indian Journal of Experimental Biology . 44 . 2 . 157–162 . 16480184.
6. 10.1021/ar000194n. 12379138. Masked o-Benzoquinones in Organic Synthesis. Accounts of Chemical Research. 35. 10. 856–866. 2002. Liao. Chun-Chen. Peddinti. Rama Krishna.
7. Teuber HJ . Use of Dipotassium Nitrosodisulfonate (Frémy's Salt): 4,5-Dimethyl-o-Benzoquinone . 10.15227/orgsyn.052.0088. 52 . 88 . 1972. Org. Synth..
8. 10.1021/ja0214274 . Synthesis and Characterization of Model Compounds of the Lysine Tyrosyl Quinone Cofactor of Lysyl Oxidase . 2003 . Mure . Minae . Wang . Sophie X. . Klinman . Judith P. . Journal of the American Chemical Society . 125 . 20 . 6113–6125 . 12785842.