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]
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.[5]
Preparation and reactionsedit
1,2-Benzoquinone is produced on oxidation of catechol exposed to air in aqueous solution[6] or by ortho oxidation of a phenol.[6]
^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.
^ abMagdziak, 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. PMC1557836. 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.
^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.
January 01, 1970
benzoquinone, also, called, ortho, benzoquinone, organic, compound, with, formula, c6h4o2, isomers, quinone, other, being, benzoquinone, volatile, solid, that, soluble, water, ethyl, ether, rarely, encountered, because, instability, fundamental, interest, pare. 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 1 2 Benzoquinone Names Preferred IUPAC name Cyclohexa 3 5 diene 1 2 dione 1 Other names ortho Benzoquinoneo Benzoquinoneo Quinone Identifiers CAS Number 583 63 1 Y 3D model JSmol Interactive imageInteractive image 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 YKey WOAHJDHKFWSLKE UHFFFAOYSA N YInChI 1 C6H4O2 c7 5 3 1 2 4 6 5 8 h1 4HKey WOAHJDHKFWSLKE UHFFFAOYAR SMILES O C1 C C C C C1 OC1 CC O C O C C1 Properties Chemical formula C 6H 4O 2 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 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 verify what is Y N Infobox references Contents 1 Structure 2 Preparation and reactions 3 Occurrence of ortho quinones 4 See also 5 ReferencesStructure editThe 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 A are characteristic of ketones 5 Preparation and reactions edit1 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 edit nbsp 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 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 See also edit1 4 BenzoquinoneReferences edit 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 Fremy 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 Retrieved from https en wikipedia org w index php title 1 2 Benzoquinone amp oldid 1199646006, wikipedia, wiki, book, books, library,
