| Revision as of 18:26, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 476909080 of page 5,8-Dihydroxy-1,4-naphthoquinone for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 07:20, 7 January 2022 edit JJMC89 bot III (talk | contribs)Bots, Administrators3,683,256 editsm Moving Category:3-hydroxypropenals within hydroxyquinones to Category:3-Hydroxypropenals within hydroxyquinones per Misplaced Pages:Categories for discussion/Speedy |
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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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| Verifiedfields = changed |
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| verifiedrevid = 413275419 |
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| verifiedrevid = 477223926 |
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| ImageFile = Naphthazarin.svg |
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| ImageFile = Naphthazarin.svg |
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| ImageSize = 130 |
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| ImageSize = 130 |
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| ImageSize1 = 180 |
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| ImageSize1 = 180 |
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| ImageName1 = Ball-and-stick model |
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| ImageName1 = Ball-and-stick model |
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| IUPACName = 5,8-dihydroxynaphthalene-1,4-dione |
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| PIN = 5,8-Dihydroxynaphthalene-1,4-dione |
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| OtherNames = Dihydroxynaphthoquinone |
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| OtherNames = Dihydroxynaphthoquinone |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| InChI = 1/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H |
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| InChI = 1/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H |
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| InChIKey = RQNVIKXOOKXAJQ-UHFFFAOYAN |
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| InChIKey = RQNVIKXOOKXAJQ-UHFFFAOYAN |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 274056 |
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| ChEMBL = 274056 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 28849 |
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| EINECS = 207-495-4 |
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| KEGG = C01938 |
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| UNII = S9IX5I5C0K |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H |
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| StdInChI = 1S/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = RQNVIKXOOKXAJQ-UHFFFAOYSA-N |
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| StdInChIKey = RQNVIKXOOKXAJQ-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|changed|CAS}} |
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| CASNo = |
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| CASNo = 475-38-7 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 9735 |
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| ChemSpiderID = 9735 |
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| PubChem = 10141 |
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| PubChem = 10141 |
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| SMILES = C1=CC(=C2C(=O)C=CC(=O)C2=C1O)O }} |
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| SMILES = C1=CC(=C2C(=O)C=CC(=O)C2=C1O)O }} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=10|H=6|O=4 |
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| Formula = C<sub>10</sub>H<sub>6</sub>O<sub>4</sub> |
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| MolarMass = 190.15 g/mol |
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| Appearance = |
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| Appearance = |
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| Density = |
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| Density = |
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| MeltingPt = |
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| MeltingPtC = 228-232 |
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| BoilingPt = |
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| BoilingPt = |
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| Solubility = }} |
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| Solubility = }} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|302|312|315|319|332|335}} |
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| PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+312|304+340|305+351+338|312|321|322|330|332+313|337+313|362|363|403+233|405|501}} |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = }} |
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| AutoignitionPt = }} |
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}} |
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}} |
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'''Naphthazarin''', often called '''5,8-dihydroxy-1,4-naphthoquinone''' or '''5,8-dihydroxy-1,4-naphthalenedione''' (]), is a naturally occurring<ref name=thomson71>Thomson R.H. Naturally Occurring Quinones. Academic Press, London (1971). Quoted by Khalafy and Bruce.</ref><ref name=thomson87>Thomson R.H. Naturally Occurring Quinones III. Chapman and Hall, London (1987). Quoted by Khalafy and Bruce. |
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</ref> ] with formula {{chem|C|10|H|6|O|4}}, formally derived from ] through replacement of two ] atoms by ] (OH) groups. It is thus one of many ] ]s. |
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Naphthazarin is soluble in ] from which it crystallizes as deep red needles that melt at 228−232 °C.<ref name=khalafy/> |
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== Synthesis == |
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Naphtharazin can be prepared by condensation of ] with ] followed by reductive ] and re].<ref name=lewis>Lewis J.R. and Paul J.J.(1977). Z. Naturforsch., B, 32: 1473. Quoted by Khalafy and Bruce.</ref><ref name=huot>Huot R. and Brassard P. (1974). Can. J. Chem., 52: 838. Quoted by Khalafy and Bruce.</ref> |
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Naphtharazin can also be obtained by oxidation of ] with ] (MnO<sub>2</sub>).<ref name=khalafy>J. Khalafy and J.M. Bruce (2002), ''Oxidative dehydrogenation of 1-tetralones: Synthesis of juglone, naphthazarin, and α-hydroxyanthraquinones''. Journal of Sciences, Islamic Republic of Iran, volume 13 issue 2, pages 131-139.</ref> |
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== References == |
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{{reflist}} |
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