4,4'-Dihydroxybenzophenone

From Wikipedia, the free encyclopedia
  (Redirected from (HOC6H4)2CO)
Jump to: navigation, search
4,4'-Dihydroxybenzophenone
Dihydroxybenzophenone.svg
Names
Other names
Benzophenone, 4,4’dihydroxy-(7Cl,8Cl); 4,4’-dihydroxydiphenyl ketone; Bis(4-hydroxyphenyl) ketone; HBP; HBP (ketone); NSC
Identifiers
3D model (JSmol)
ChemSpider
DrugBank
ECHA InfoCard 100.009.354
KEGG
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
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).
N verify (what is YesYN ?)
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[edit]

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[edit]

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[edit]

  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