4,4'-Dihydroxybenzophenone (original) (raw)
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4,4′-Dihydroxybenzophenone
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| Names | |
| Preferred IUPAC name Bis(4-hydroxyphenyl)methanone | |
| Other namesBenzophenone, 4,4′-dihydroxy-(7Cl,8Cl); 4,4′-dihydroxydiphenyl ketone; Bis(4-hydroxyphenyl) ketone; HBP; HBP (ketone); NSC | |
| Identifiers | |
| CAS Number | 611-99-4  N |
| 3D model (JSmol) | Interactive image |
| ChEBI | CHEBI:34365 |
| ChEMBL | ChEMBL194859  Y |
| ChemSpider | 62365 Y |
| DrugBank | DB07635 Y |
| ECHA InfoCard | 100.009.354  |
| EC Number | 210-288-1 |
| KEGG | C14220 Y |
| PubChem CID | 69150 |
| UNII | HZR7D31SBY |
| CompTox Dashboard (EPA) | DTXSID1022425 |
| InChI InChI=1S/C13H10O3/c14-11-5-1-9(2-6-11)13(16)10-3-7-12(15)8-4-10/h1-8,14-15H YKey: RXNYJUSEXLAVNQ-UHFFFAOYSA-N YInChI=1/C13H10O3/c14-11-5-1-9(2-6-11)13(16)10-3-7-12(15)8-4-10/h1-8,14-15HKey: RXNYJUSEXLAVNQ-UHFFFAOYAR |
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| SMILES O=C(c1ccc(O)cc1)c2ccc(O)cc2 | |
| Properties | |
| Chemical formula | C13H10O3 |
| Molar mass | 214.22 g/mol |
| Appearance | Off white/yellow solid |
| Density | 1.302g/cm3 |
| Melting point | 213 to 215 °C (415 to 419 °F; 486 to 488 K) |
| Boiling point | 444.8 °C (832.6 °F; 718.0 K) @760mmHg |
| Solubility in water | 0.45 g/L |
| Hazards | |
| GHS labelling: | |
| Pictograms |  |
| Signal word | Warning |
| Hazard statements | H315, H317, H319, H335 |
| Precautionary statements | P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501 |
| Flash point | 237 °C (459 °F; 510 K) |
| Safety data sheet (SDS) | MSDS by Fisher Scientific |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).  N verify (what is YN ?) Infobox references |
Chemical compound
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.[1]
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.
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.[2]
- ^ Eddine, Ali Nasser; von Kries, Jens P.; Podust, Mikhail V.; Warrier, Thulasi; Kaufmann, Stefan H. E.; Podust, Larissa M. (2008). "X-ray structure of 4,4′-dihydroxybenzophenone mimicking sterol substrate in the active site of sterol 14α-demethylase (CYP51)". Journal of Biological Chemistry. 283 (22): 15152–15159. doi:10.1074/jbc.M801145200. PMC 2397474. PMID 18367444. S2CID 22025443.
- ^ 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