4,4'-Dihydroxybenzophenone
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]
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Other names
Benzophenone, 4,4’dihydroxy-(7Cl,8Cl); 4,4’-dihydroxydiphenyl ketone; Bis(4-hydroxyphenyl) ketone; HBP; HBP (ketone); NSC | |
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DrugBank | |
ECHA InfoCard | 100.009.354 |
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Properties | |
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 |
0.45 g/L | |
Hazards | |
Safety data sheet | MSDS by Fisher Scientific |
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GHS Signal word | Warning |
GHS hazard statements |
H315, H317, H319, H335 |
P261, P264, P271, P272, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P333+313, P337+313, P362, P363, P403+233, P405, P501 | |
Flash point | 237 °C (459 °F; 510 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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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.[2]
McMurry reaction between CHone and p,p'-dihydroxybenzophenone, and subsequent acetylation gives Cyclofenil.
References
- Eddine, Ali Nasser; von Kries, Jens P.; Podust, Mikhail V.; Warrier, Thulasi; Kaufmann, Stefan H. E.; Podust, Larissa M. "X-ray Structure of 4, 4 '- Dihydroxybenzophenone Mimicking Sterol Substrate in the Active Site of Sterol 14a -Demethylase (CYP51)" Journal of Biological Chemistry (2008), 283, pp. 15152-15159. doi:10.1074/jbc.M801145200
- 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