| Revision as of 18:04, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465356638 of page 4,4'-Dihydroxybenzophenone for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 10:04, 21 October 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Phenols; added Category:4-Hydroxyphenyl compounds using HotCat |
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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 = 413270218 |
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| verifiedrevid = 477220615 |
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| Name = 4,4'-Dihydroxybenzophenone |
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| Name = 4,4′-Dihydroxybenzophenone |
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| ImageFile = Dihydroxybenzophenone.svg |
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| ImageFile = Dihydroxybenzophenone.svg |
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| OtherNames = Benzophenone, 4,4’dihydroxy-(7Cl,8Cl); 4,4’-dihydroxydiphenyl ketone; Bis(4-hydroxyphenyl) ketone; HBP; HBP (ketone); NSC |
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| PIN = Bis(4-hydroxyphenyl)methanone |
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| OtherNames = Benzophenone, 4,4′-dihydroxy-(7Cl,8Cl); 4,4′-dihydroxydiphenyl ketone; Bis(4-hydroxyphenyl) ketone; HBP; HBP (ketone); NSC |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 62365 |
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| ChemSpiderID = 62365 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| InChI = 1/C13H10O3/c14-11-5-1-9(2-6-11)13(16)10-3-7-12(15)8-4-10/h1-8,14-15H |
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| InChI = 1/C13H10O3/c14-11-5-1-9(2-6-11)13(16)10-3-7-12(15)8-4-10/h1-8,14-15H |
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| InChIKey = RXNYJUSEXLAVNQ-UHFFFAOYAR |
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| InChIKey = RXNYJUSEXLAVNQ-UHFFFAOYAR |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB07635 |
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| DrugBank = DB07635 |
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| PubChem = 69150 |
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| EC_number = 210-288-1 |
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| UNII = HZR7D31SBY |
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| SMILES = O=C(c1ccc(O)cc1)c2ccc(O)cc2 |
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| SMILES = O=C(c1ccc(O)cc1)c2ccc(O)cc2 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 194859 |
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| ChEMBL = 194859 |
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| ChEBI = 34365 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C13H10O3/c14-11-5-1-9(2-6-11)13(16)10-3-7-12(15)8-4-10/h1-8,14-15H |
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| StdInChI = 1S/C13H10O3/c14-11-5-1-9(2-6-11)13(16)10-3-7-12(15)8-4-10/h1-8,14-15H |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = RXNYJUSEXLAVNQ-UHFFFAOYSA-N |
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| StdInChIKey = RXNYJUSEXLAVNQ-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = <!-- blanked - oldvalue: 611-99-4 --> |
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| CASNo = 611-99-4 |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>13</sub>H<sub>10</sub>O<sub>3</sub> |
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| Formula = C<sub>13</sub>H<sub>10</sub>O<sub>3</sub> |
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| MolarMass = 214.22 g/mol |
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| Appearance = Off white/yellow solid |
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| MolarMass = 214.22 g/mol |
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| Appearance = Off white/yellow solid |
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| Solubility = 0.45 g/L |
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| Solubility = 0.45 g/L |
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| MeltingPtC = 213 to 215 |
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| MeltingPt = 213–215 °C |
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| MeltingPt_notes = |
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| BoilingPt = 444.8 °C @760mmHg |
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| Density = 1.302g/cm3 |
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| BoilingPtC = 444.8 |
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| BoilingPt_notes = @760mmHg |
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| Density = 1.302g/cm3 |
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}} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| FlashPt = 237 °C |
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| FlashPtC = 237 |
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| ExternalMSDS = |
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| ExternalSDS = |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|315|317|319|335}} |
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| PPhrases = {{P-phrases|261|264|271|272|280|302+352|304+340|305+351+338|312|321|332+313|333+313|337+313|362|363|403+233|405|501}} |
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'''4,4′-Dihydroxybenzophenone''' is an ] with the formula (HOC<sub>6</sub>H<sub>4</sub>)<sub>2</sub>CO. This off-white solid is a precursor to, or a degradation product of, diverse commercial materials. It is a potential ].<ref>{{cite journal |last1=Eddine |first1=Ali Nasser |last2=von Kries |first2=Jens P. |last3=Podust |first3=Mikhail V. |last4=Warrier |first4=Thulasi |last5=Kaufmann |first5=Stefan H. E. |last6=Podust |first6=Larissa M. |date=2008 |title=X-ray structure of 4,4′-dihydroxybenzophenone mimicking sterol substrate in the active site of sterol 14α-demethylase (CYP51) |title-link=doi |journal=Journal of Biological Chemistry |volume=283 |issue=22 |pages=15152–15159 |doi=10.1074/jbc.M801145200 |pmc=2397474 |pmid=18367444 |doi-access=free |s2cid=22025443 |s2cid-access=free}}</ref> |
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== Synthesis == |
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4,4′-Dihydroxybenzophenone is prepared by the ] of ''p''-hydroxyphenylbenzoate: |
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:HOC<sub>6</sub>H<sub>4</sub>CO<sub>2</sub>C<sub>6</sub>H<sub>5</sub> → (HOC<sub>6</sub>H<sub>4</sub>)<sub>2</sub>CO |
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Alternatively, ] can be converted to ''p''-acetoxybenzoyl chloride. This ] reacts with ] to give, after deacetylation, 4,4′-dihydroxybenzophenone. |
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== Uses == |
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The main application of 4,4′-dihydroxybenzophenone is as a ]. It and its derivatives are found in ], ], films, ] and coatings, ], and printed circuit boards. It is the precursor to certain ] polymers.<ref>David Parker, Jan Bussink, Hendrik T. van de Grampe, Gary W. Wheatley, Ernst-Ulrich Dorf, Edgar Ostlinning, Klaus Reinking "Polymers, High-Temperature" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2002.{{doi|10.1002/14356007.a21_449}}</ref> |
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== References == |
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<references/> |
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{{DEFAULTSORT:Dihydroxybenzophenone, 4,4'-}} |
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] |
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] |