1,2-Benzoquinone

1,2-Benzoquinone

Names

Preferred IUPAC name

Cyclohexa-3,5-diene-1,2-dione^[1]

Other names

ortho-Benzoquinone
o-Benzoquinone
o-Quinone

Identifiers

CAS Number

583-63-1^Y

3D model (JSmol)

ChEBI

CHEBI:17253^Y

ChemSpider

10941^Y

ECHA InfoCard

100.243.463

KEGG

C02351^Y

PubChem CID

11421

UNII

SVD1LJ47R7^Y

CompTox Dashboard (EPA)

DTXSID60894765

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

SMILES

O=C1/C=C\C=C/C1=O
C1=CC(=O)C(=O)C=C1

Properties

Chemical formula

C₆H₄O₂

Molar mass

108.096 g·mol⁻¹

Appearance

Red volatile solid

Density

1.424 g/cm³

Melting point

60–70 °C (140–158 °F; 333–343 K) decomposes^[2]

Hazards

Flash point

76.4 °C (169.5 °F; 349.5 K)

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).

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Infobox references

1,2-Benzoquinone, also called ortho-benzoquinone, is an organic compound with formula C₆H₄O₂. 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.^[3]^[4]

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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.^[5]

Preparation and reactions

1,2-Benzoquinone is produced on oxidation of catechol exposed to air in aqueous solution^[6] or by ortho oxidation of a phenol.^[6]

A strain of the bacterium Pseudomonas mendocina metabolises benzoic acid, yielding 1,2-benzoquinone via catechol.^[7]

Ortho-quinones are widely used in organic synthesis.^[8]

Occurrence of ortho-quinones

4,5-Dimethyl-1,2-benzoquinone, also a red solid, is a well behaved synthetic ortho-quinone.^[9]

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.^[10]

References

^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 728. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ Eagleson, Mary (1994). Concise encyclopedia chemistry. Berlin: Walter de Gruyter. p. 123. ISBN 0-89925-457-8. OCLC 29029713.
^ Patai, Saul, ed. (1974). Quinonoid Compounds: Vol. 1 (1974). PATAI'S Chemistry of Functional Groups. doi:10.1002/9780470771297. ISBN 9780470771297.
^ Patai, Saul, ed. (1974). Quinonoid Compounds: Vol. 2 (1974). PATAI'S Chemistry of Functional Groups. doi:10.1002/9780470771303. ISBN 9780470771303.
^ MacDonald, Alistair L.; Trotter, James (1973). "Crystal and molecular structure of o-benzoquinone". Journal of the Chemical Society, Perkin Transactions 2 (4): 476. doi:10.1039/P29730000476.
^ ^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.
^ Chanda Parulekar and Suneela Mavinkurve (2006). "Formation of ortho-benzoquinone from sodium benzoate by Pseudomonas mendocina P₂d" (PDF). Indian Journal of Experimental Biology. 44 (2): 157–162. PMID 16480184.
^ Liao, Chun-Chen; Peddinti, Rama Krishna (2002). "Masked o-Benzoquinones in Organic Synthesis". Accounts of Chemical Research. 35 (10): 856–866. doi:10.1021/ar000194n. PMID 12379138.
^ Teuber HJ (1972). "Use of Dipotassium Nitrosodisulfonate (Frémy's Salt): 4,5-Dimethyl-o-Benzoquinone". Org. Synth. 52: 88. doi:10.15227/orgsyn.052.0088.
^ Mure, Minae; Wang, Sophie X.; Klinman, Judith P. (2003). "Synthesis and Characterization of Model Compounds of the Lysine Tyrosyl Quinone Cofactor of Lysyl Oxidase". Journal of the American Chemical Society. 125 (20): 6113–6125. doi:10.1021/ja0214274. PMID 12785842.

This page was last edited on 27 January 2024, at 16:03

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