Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Naphthazarin: Difference between pages
(Difference between pages)
Content deleted Content added
Saving copy of the {{chembox}} taken from revid 476909080 of page 5,8-Dihydroxy-1,4-naphthoquinone for the Chem/Drugbox validation project (updated: ''). |
m Moving Category:3-hydroxypropenals within hydroxyquinones to Category:3-Hydroxypropenals within hydroxyquinones per Wikipedia:Categories for discussion/Speedy |
||
| Line 1: | Line 1: | ||
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:5,8-Dihydroxy-1,4-naphthoquinone|oldid=476909080}} 476909080] of page [[5,8-Dihydroxy-1,4-naphthoquinone]] with values updated to verified values.}} |
|||
{{chembox |
{{chembox |
||
| Verifiedfields = changed |
|||
| verifiedrevid = |
| verifiedrevid = |
||
| ImageFile = Naphthazarin.svg |
| ImageFile = Naphthazarin.svg |
||
| ImageSize = 130 |
| ImageSize = 130 |
||
| Line 8: | Line 8: | ||
| ImageSize1 = 180 |
| ImageSize1 = 180 |
||
| ImageName1 = Ball-and-stick model |
| ImageName1 = Ball-and-stick model |
||
| |
| = 5,8--1,4-dione |
||
| OtherNames = Dihydroxynaphthoquinone |
| OtherNames = Dihydroxynaphthoquinone |
||
| |
|Section1={{Chembox Identifiers |
||
| InChI = 1/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H |
| InChI = 1/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H |
||
| InChIKey = RQNVIKXOOKXAJQ-UHFFFAOYAN |
| InChIKey = RQNVIKXOOKXAJQ-UHFFFAOYAN |
||
| Line 16: | Line 16: | ||
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
||
| ChEMBL = 274056 |
| ChEMBL = 274056 |
||
| ChEBI_Ref = {{ebicite|changed|EBI}} |
|||
| ChEBI = 28849 |
|||
| EINECS = 207-495-4 |
|||
| KEGG = C01938 |
|||
| UNII = S9IX5I5C0K |
|||
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
||
| StdInChI = 1S/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H |
| StdInChI = 1S/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H |
||
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
||
| StdInChIKey = RQNVIKXOOKXAJQ-UHFFFAOYSA-N |
| StdInChIKey = RQNVIKXOOKXAJQ-UHFFFAOYSA-N |
||
| CASNo_Ref = {{cascite| |
| CASNo_Ref = {{cascite||}} |
||
| CASNo = |
| CASNo = |
||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
||
| ChemSpiderID = 9735 |
| ChemSpiderID = 9735 |
||
| PubChem = 10141 |
| PubChem = 10141 |
||
| SMILES = C1=CC(=C2C(=O)C=CC(=O)C2=C1O)O }} |
| SMILES = C1=CC(=C2C(=O)C=CC(=O)C2=C1O)O }} |
||
| |
|Section2={{Chembox Properties |
||
| C=10|H=6|O=4 |
|||
| Formula = C<sub>10</sub>H<sub>6</sub>O<sub>4</sub> |
|||
| MolarMass = 190.15 g/mol |
|||
| Appearance = |
| Appearance = |
||
| Density = |
| Density = |
||
| |
| = |
||
| BoilingPt = |
| BoilingPt = |
||
| Solubility = }} |
| Solubility = }} |
||
| |
|Section3={{Chembox Hazards |
||
| GHSPictograms = {{GHS07}} |
|||
| GHSSignalWord = Warning |
|||
| HPhrases = {{H-phrases|302|312|315|319|332|335}} |
|||
| 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}} |
|||
| MainHazards = |
| MainHazards = |
||
| FlashPt = |
| FlashPt = |
||
| |
| = }} |
||
}} |
}} |
||
'''Naphthazarin''', often called '''5,8-dihydroxy-1,4-naphthoquinone''' or '''5,8-dihydroxy-1,4-naphthalenedione''' ([[IUPAC]]), 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. |
|||
</ref> [[organic compound]] with formula {{chem|C|10|H|6|O|4}}, formally derived from [[1,4-naphthoquinone]] through replacement of two [[hydrogen]] atoms by [[hydroxyl]] (OH) groups. It is thus one of many [[dihydroxynaphthoquinone]] [[structural isomer]]s. |
|||
Naphthazarin is soluble in [[1,4-dioxane]] from which it crystallizes as deep red needles that melt at 228−232 °C.<ref name=khalafy/> |
|||
== Synthesis == |
|||
Naphtharazin can be prepared by condensation of [[1,4-dimethoxybenzene]] with [[2,3-dichloromaleic anhydride]] followed by reductive [[dechlorination]] and re[[oxidation]].<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> |
|||
Naphtharazin can also be obtained by oxidation of [[5,8-dihydroxy-1-tetralone]] with [[manganese dioxide]] (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> |
|||
== References == |
|||
{{reflist}} |
|||
[[Category:1,4-Naphthoquinones]] |
|||
[[Category:Hydroquinones]] |
|||
[[Category:Hydroxynaphthoquinones]] |
|||
[[Category:3-Hydroxypropenals within hydroxyquinones]] |
|||