4,4'-Dihydroxybenzophenone
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477220615
| Name = 4,4′-Dihydroxybenzophenone
| ImageFile = Dihydroxybenzophenone.svg
| PIN = Bis(4-hydroxyphenyl)methanone
| OtherNames = Benzophenone, 4,4′-dihydroxy-(7Cl,8Cl); 4,4′-dihydroxydiphenyl ketone; Bis(4-hydroxyphenyl) ketone; HBP; HBP (ketone); NSC
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 62365
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C14220
| 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
| InChIKey = RXNYJUSEXLAVNQ-UHFFFAOYAR
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB07635
| PubChem = 69150
| EC_number = 210-288-1
| UNII = HZR7D31SBY
| SMILES = O=C(c1ccc(O)cc1)c2ccc(O)cc2
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 194859
| ChEBI = 34365
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RXNYJUSEXLAVNQ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 611-99-4
}}
|Section2={{Chembox Properties
| Formula = C13H10O3
| MolarMass = 214.22 g/mol
| Appearance = Off white/yellow solid
| Solubility = 0.45 g/L
| MeltingPtC = 213 to 215
| MeltingPt_notes =
| BoilingPtC = 444.8
| BoilingPt_notes = @760mmHg
| Density = 1.302g/cm3
}}
|Section3={{Chembox Hazards
| FlashPtC = 237
| ExternalSDS = [https://fscimage.fishersci.com/msds/81424.htm MSDS by Fisher Scientific]
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|317|319|335}}
| 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}}
}}
}}
4,4′-Dihydroxybenzophenone is an organic compound with the formula (HOC6H4)2CO. This off-white solid is a precursor to, or a degradation product of, diverse commercial materials. It is a potential endocrine disruptor.{{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}}
Synthesis
4,4′-Dihydroxybenzophenone is prepared by the rearrangement of p-hydroxyphenylbenzoate:
:HOC6H4CO2C6H5 → (HOC6H4)2CO
Alternatively, p-hydroxybenzoic acid can be converted to p-acetoxybenzoyl chloride. This acid chloride reacts with phenol to give, after deacetylation, 4,4′-dihydroxybenzophenone.
Uses
The main application of 4,4′-dihydroxybenzophenone is as a UV light stabilizer. It and its derivatives are found in cosmetics, plastics, films, adhesives and coatings, optical fiber, and printed circuit boards. It is the precursor to certain polycarbonate polymers.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}}
References
{{DEFAULTSORT:Dihydroxybenzophenone, 4,4'-}}