1,2-Benzoquinone

Chemical compound changed changed 477202978 Orthobenzoquinone.svg 1,2-benzoquinone-3D-vdW.png Cyclohexa-3,5-diene-1,2-dione Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) The Royal Society of Chemistry 2014 Cambridge 728 10.1039/9781849733069-FP001 978-0-85404-182-4 ortho-Benzoquinone o-Benzoquinone o-Quinone correct kegg C02351 1/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4H WOAHJDHKFWSLKE-UHFFFAOYAR C1=CC(=O)C(=O)C=C1 correct chemspider 1S/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4H correct chemspider WOAHJDHKFWSLKE-UHFFFAOYSA-N correct ?? 583-63-1 11421 correct FDA SVD1LJ47R7 O=C1/C=C\C=C/C1=O correct chemspider correct EBI 17253 10941 6 4 2 Red volatile solid 1.424 g/cm3 60-70 decomposesEagleson Mary Concise encyclopedia chemistry Walter de Gruyter Berlin 1994 0-89925-457-8 29029713 123 76.4 1,4-benzoquinone quinone 1,2-Benzoquinone, also called ortho-benzoquinone, is an organic compound with formula C6H4O2 yes. 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.10.1002/9780470771297 Quinonoid Compounds: Vol. 1 (1974) 1974 9780470771297 Patai Saul PATAI'S Chemistry of Functional Groups10.1002/9780470771303 Quinonoid Compounds: Vol. 2 (1974) 1974 9780470771303 Patai Saul PATAI'S Chemistry of Functional Groups Structure The molecule has C2v 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. 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 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.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) Org. Lett. 4 2 285–288 2002 10.1021/ol017068j 1557836 11796071 A strain of the bacterium Pseudomonas mendocina metabolises benzoic acid, yielding 1,2-benzoquinone via catechol. 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 http://nopr.niscair.res.in/bitstream/123456789/6370/1/IJEB%2044(2)%20157-162.pdf 16480184 Ortho-quinones are widely used in organic synthesis. 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 Occurrence of ortho-quinones thumb|The oxidation of lysyl side chains is effected in nature by the action of an orthoquinone called lysyl tyrosylquinone.|center|420 px 4,5-Dimethyl-1,2-benzoquinone, also a red solid, is a well behaved synthetic ortho-quinone. Teuber HJ Use of Dipotassium Nitrosodisulfonate (Frémy's Salt): 4,5-Dimethyl-o-Benzoquinone 10.15227/orgsyn.052.0088 free 52 88 1972 Org. Synth. 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.10.1021/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 See also 1,4-Benzoquinone References Category:Enones ja:ベンゾキノン#1,2-ベンゾキノン