| Revision as of 16:07, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 443807729 of page 1,2-Benzoquinone for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 16:03, 27 January 2024 edit Bernardirfan (talk | contribs)Extended confirmed users10,991 edits Extra white spaces |
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{{short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 443340025 |
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| ImageFileL1 = Orthobenzoquinone.svg |
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| verifiedrevid = 477202978 |
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| ImageSizeL1 = 100px |
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| ImageFileL1 = Orthobenzoquinone.svg |
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| ImageFileR1 = 1,2-benzoquinone-3D-vdW.png |
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| ImageFileR1 = 1,2-benzoquinone-3D-vdW.png |
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| ImageSizeR1 = 120px |
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| PIN = Cyclohexa-3,5-diene-1,2-dione<ref name="IUPAC2013_728">{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 728 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref> |
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| IUPACName = cyclohexa-3,5-diene-1,2-dione |
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| OtherNames = 1,2-benzoquinone, ''o''-benzoquinone, ''o''-quinone |
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| OtherNames = {{bulletedlist|''ortho''-Benzoquinone|''o''-Benzoquinone|''o''-Quinone}} |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C02351 |
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| KEGG = C02351 |
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| InChI = 1/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4H |
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| InChI = 1/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4H |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = WOAHJDHKFWSLKE-UHFFFAOYSA-N |
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| StdInChIKey = WOAHJDHKFWSLKE-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = <!-- blanked - oldvalue: 583-63-1 --> |
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| CASNo = 583-63-1 |
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| PubChem = 11421 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 11421 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = SVD1LJ47R7 |
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| UNII = SVD1LJ47R7 |
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| SMILES = O=C1/C=C\C=C/C1=O |
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| SMILES = O=C1/C=C\C=C/C1=O |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 17253 |
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| ChEBI = 17253 |
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| ChemSpiderID=10941 |
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| ChemSpiderID =10941 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=6|H=4|O=2 |
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| Formula = C<sub>6</sub>H<sub>4</sub>O<sub>2</sub> |
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| Appearance = Red volatile solid |
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| MolarMass = 108.0964 g/mol |
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| Density = 1.424 g/cm{{sup|3}} |
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| Appearance = |
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| MeltingPtC = 60-70 |
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| Density = 1.256 g/cm3 |
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|MeltingPt_notes=decomposes<ref>{{cite book | last=Eagleson | first=Mary | title=Concise encyclopedia chemistry | publisher=Walter de Gruyter | publication-place=Berlin | date=1994 | isbn=0-89925-457-8 | oclc=29029713|page=123}}</ref> |
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| MeltingPt = |
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| Solubility = |
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| BoilingPt = 213.3 °C @760 mmHg |
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|Section7={{Chembox Hazards |
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| MainHazards = |
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| Section7 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPtC = 76.4 |
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| AutoignitionPtC = |
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| FlashPt = 76.4 °C |
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|Section8={{Chembox Related |
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| OtherCompounds = ] <br/> ] |
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| OtherCpds = ] ] |
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'''1,2-Benzoquinone''', also called '''''ortho''-benzoquinone''', is an ] with formula {{Chem2|C6H4O2|auto=yes}}. It is one of the two isomers of ], the other being ]. It is a red volatile solid that is soluble in water and ]. It is rarely encountered because of its instability, but it is of fundamental interest as the parent compound of many ] which are known.<ref>{{cite book |doi=10.1002/9780470771297 |title=Quinonoid Compounds: Vol. 1 (1974) |year=1974 |isbn=9780470771297 |editor-last1=Patai |editor-first1=Saul|series=PATAI'S Chemistry of Functional Groups}}</ref><ref>{{cite book |doi=10.1002/9780470771303 |title=Quinonoid Compounds: Vol. 2 (1974) |year=1974 |isbn=9780470771303 |editor-last1=Patai |editor-first1=Saul|series=PATAI'S Chemistry of Functional Groups}}</ref> |
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==Structure== |
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The molecule has C{{sub|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.<ref>{{cite journal | doi = 10.1039/P29730000476| title = Crystal and molecular structure of o-benzoquinone| journal = Journal of the Chemical Society, Perkin Transactions 2| issue = 4| pages = 476| year = 1973| last1 = MacDonald| first1 = Alistair L.| last2 = Trotter| first2 = James}}</ref> |
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==Preparation and reactions== |
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1,2-Benzoquinone is produced on oxidation of ] exposed to air in aqueous solution<ref name=mag/> or by ortho oxidation of a ].<ref name=mag>{{cite journal |author1=Magdziak, D. |author2=Rodriguez, A. A. |author3=Van De Water, R. W. |author4=Pettus, T. R. R. | title = Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX) | journal = ] | volume = 4 | issue = 2 | pages = 285–288 | year = 2002 | doi = 10.1021/ol017068j | pmc = 1557836 | pmid=11796071}}</ref> |
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A strain of the ] '']'' ] ], yielding 1,2-benzoquinone via ].<ref name=paru>{{Cite journal | author = Chanda Parulekar and Suneela Mavinkurve | date = 2006 | title = Formation of ''ortho''-benzoquinone from sodium benzoate by ''Pseudomonas mendocina'' P<sub>2</sub>d | journal = Indian Journal of Experimental Biology | volume = 44 | issue = 2 | pages = 157–162 | url = http://nopr.niscair.res.in/bitstream/123456789/6370/1/IJEB%2044(2)%20157-162.pdf | pmid = 16480184}}</ref> |
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Ortho-quinones are widely used in ].<ref>{{cite journal | doi = 10.1021/ar000194n| pmid = 12379138| title = Masked o-Benzoquinones in Organic Synthesis| journal = Accounts of Chemical Research| volume = 35| issue = 10| pages = 856–866| year = 2002| last1 = Liao| first1 = Chun-Chen| last2 = Peddinti| first2 = Rama Krishna}}</ref> |
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==Occurrence of ''ortho''-quinones== |
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] is effected in nature by the action of an orthoquinone called lysyl tyrosylquinone.|center|420 px]] |
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4,5-Dimethyl-1,2-benzoquinone, also a red solid, is a well behaved synthetic ''ortho''-quinone.<ref>{{cite journal| vauthors = Teuber HJ | title = Use of Dipotassium Nitrosodisulfonate (Frémy's Salt): 4,5-Dimethyl-''o''-Benzoquinone | doi= 10.15227/orgsyn.052.0088| volume= 52 | page= 88 | year = 1972|journal=Org. Synth.}}</ref> |
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The biological pigment ] is rich in ''ortho''-quinones. |
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Finally, the enzyme ] ] (TTQ), ] (CTQ), ] (LTQ) and ] (PQQ) contain the ''ortho''-quinone moiety in their chemical structure.<ref>{{cite journal |doi=10.1021/ja0214274 |title=Synthesis and Characterization of Model Compounds of the Lysine Tyrosyl Quinone Cofactor of Lysyl Oxidase |year=2003 |last1=Mure |first1=Minae |last2=Wang |first2=Sophie X. |last3=Klinman |first3=Judith P. |journal=Journal of the American Chemical Society |volume=125 |issue=20 |pages=6113–6125 |pmid=12785842}}</ref><!--this ref to be replaced by review--> |
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==See also== |
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*] |
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== References == |
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{{reflist}} |
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{{DEFAULTSORT:Benzoquinone, 1, 2-}} |
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] |
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] |
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] |