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]

4,4′-Dihydroxybenzophenone
Names
Preferred IUPAC name
Bis(4-hydroxyphenyl)methanone
Other names
Benzophenone, 4,4′-dihydroxy-(7Cl,8Cl); 4,4′-dihydroxydiphenyl ketone; Bis(4-hydroxyphenyl) ketone; HBP; HBP (ketone); NSC
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.009.354
EC Number
  • 210-288-1
KEGG
UNII
  • 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 checkY
    Key: RXNYJUSEXLAVNQ-UHFFFAOYSA-N checkY
  • 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
    Key: RXNYJUSEXLAVNQ-UHFFFAOYAR
  • O=C(c1ccc(O)cc1)c2ccc(O)cc2
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
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H317, H319, H335
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 checkY☒N ?)
Infobox references

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]

References
  1. 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.
  2. 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
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