4,4'-Dihydroxybenzophenone

4,4'-Dihydroxybenzophenone
Other names Benzophenone, 4,4’dihydroxy-(7Cl,8Cl); 4,4’-dihydroxydiphenyl ketone; Bis(4-hydroxyphenyl) ketone; HBP; HBP (ketone); NSC
Identifiers
CAS number	611-99-4
ChemSpider	62365 Y
DrugBank	DB07635
KEGG	C14220 Y
ChEMBL	CHEMBL194859 Y
Jmol-3D images	Image 1
SMILES O=C(c1ccc(O)cc1)c2ccc(O)cc2
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 Y Key: RXNYJUSEXLAVNQ-UHFFFAOYSA-N Y 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
Properties
Molecular formula	C13H10O3
Molar mass	214.22 g/mol
Appearance	Off white/yellow solid
Density	1.302g/cm3
Melting point	213-215 °C
Boiling point	444.8 °C @760mmHg
Solubility in water	0.45 g/L
Hazards
MSDS	MSDS by Fisher Scientific
Flash point	237 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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]

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. "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
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