Bisphenol AF

Bisphenol AF (BPAF) is a fluorinated organic compound that is an analogue of bisphenol A in which the two methyl groups are replaced with trifluoromethyl groups. It exists as a white to light-gray powder.

Bisphenol AF
Names
Preferred IUPAC name
4,4′-(1,1,1,3,3,3-Hexafluoropropane-2,2-diyl)diphenol
Other names
Biphenol AF; Hexafluorobisphenol A; Hexafluorodiphenylolpropane; Bisphenol A hexafluoride; 4,4'-(Hexafluoroisopropylidene)diphenol; Hexafluoroacetone bisphenol A; 2,2-Bis(4-hydroxyphenyl)hexafluoropropane
Identifiers
3D model (JSmol)
Abbreviations BPAF
ChemSpider
ECHA InfoCard 100.014.579
UNII
  • InChI=1S/C15H10F6O2/c16-14(17,18)13(15(19,20)21,9-1-5-11(22)6-2-9)10-3-7-12(23)8-4-10/h1-8,22-23H checkY
    Key: ZFVMWEVVKGLCIJ-UHFFFAOYSA-N checkY
  • InChI=1/C15H10F6O2/c16-14(17,18)13(15(19,20)21,9-1-5-11(22)6-2-9)10-3-7-12(23)8-4-10/h1-8,22-23H
    Key: ZFVMWEVVKGLCIJ-UHFFFAOYAS
  • C1=CC(=CC=C1C(C2=CC=C(C=C2)O)(C(F)(F)F)C(F)(F)F)O
Properties
C15H10F6O2
Molar mass 336.233 g·mol−1
Melting point 162 °C[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Biological and Chemical Action
Further information: endocrine disruptor

Bisphenol AF is an endocrine disrupting chemical.[2] Whereas BPA binds with human estrogen-related receptor gamma (ERR-γ), BPAF all but ignores ERR-γ. Instead, BPAF activates ERR-α and binds to and disables ERR-β.[3]

The chemical shifts in 1H, 13C and 19F NMR spectroscopy are given in the literature.[4]

Applications

Bisphenol AF is used as a crosslinking agent for certain fluoroelastomers and as a monomer for polyimides, polyamides, polyesters, polycarbonate copolymers and other specialty polymers. Polymers containing Bisphenol AF are useful in specialties such as high-temperature composites and electronic materials. Industries include cosmetics, chemical manufacturing, production of metals and rubber. It can also be a plastic additive.[5]

See also

References
  1. Hayasaka, Tatsuya; Katsuhara, Yutaka; Kume, Takashi; Yamazaki, Takashi (2011). "HF-mediated equilibrium between fluorinated ketones and the corresponding α-fluoroalcohols". Tetrahedron. 67 (12): 2215–2219. doi:10.1016/j.tet.2011.01.087.
  2. Escrivá, Laura; Hanberg, Annika; Zilliacus, Johanna; Beronius, Anna (September 2019). "Assessment of the endocrine disrupting properties of Bisphenol AF according to the EU criteria and ECHA/EFSA guidance". EFSA Journal. 17 (EU‐FORA: Series 2): e170914. doi:10.2903/j.efsa.2019.e170914. PMC 7015508. PMID 32626472.
  3. "Janet Raloff: Another plastics ingredient raises safety concerns, Science News, June 5th, 2010; Vol.177 #12 (p. 14)". Archived from the original on 2012-09-27. Retrieved 2010-06-11.
  4. Hayasaka, Tatsuya; Katsuhara, Yutaka; Kume, Takashi; Yamazaki, Takashi (2011). "HF-mediated equilibrium between fluorinated ketones and the corresponding α-fluoroalcohols". Tetrahedron. 67 (12): 2215–2219. doi:10.1016/j.tet.2011.01.087.
  5. "Bisphenol AF". PubChem. National Library of Medicine. Retrieved 20 January 2021.
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