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4,4'-Difluorobenzophenone

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4,4'-Difluorobenzophenone
Names
Preferred IUPAC name Bis(4-fluorophenyl)methanone
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.005.879 Edit this at Wikidata
EC Number
  • 206-466-3
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C13H8F2O/c14-11-5-1-9(2-6-11)13(16)10-3-7-12(15)8-4-10/h1-8HKey: LSQARZALBDFYQZ-UHFFFAOYSA-N
  • InChI=1/C13H8F2O/c14-11-5-1-9(2-6-11)13(16)10-3-7-12(15)8-4-10/h1-8HKey: LSQARZALBDFYQZ-UHFFFAOYAZ
SMILES
  • O=C(c1ccc(F)cc1)c2ccc(F)cc2
Properties
Chemical formula C13H8OF2
Molar mass 218.20 g/mol
Appearance Colorless Solid
Melting point 107.5 to 108.5 °C (225.5 to 227.3 °F; 380.6 to 381.6 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS09: Environmental hazard
Signal word Warning
Hazard statements H302, H315, H319, H335, H411
Precautionary statements P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

4,4’-Difluorobenzophenone is an organic compound with the formula of (FC6H4)2CO. This colorless solid is commonly used as a precursor to PEEK, or polyetherether ketone, a so-called high performance polymer. Because PEEK is resistant to attack, it is commonly used in carbon fiber coatings and cable insulation.

Synthesis

4,4’-Difluorobenzophenone is prepared by the acylation of fluorobenzene with p-fluorobenzoyl chloride. The conversion is typically conducted in the presence of an aluminium chloride catalyst in a petroleum ether solvent.

FC6H4C(O)Cl + C6H5F → (FC6H4)2CO + HCl

Uses

The polymer PEEK is generated from the reaction of 4,4'-difluorobenzophenone with the salts of 1,4-benzenediol.

C6H4(ONa)2 + (FC6H4)2CO → 1/nn + 2 NaF

References

  1. R.D. Dunlop and John H. Gardner (1933). "Preparation of Fluorbenzophenones". J. Am. Chem. Soc. 55 (4): 1665–1666. doi:10.1021/ja01331a058.
  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.
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