Bisphenol AF

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title: "Bisphenol AF" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["2,2-bis(4-hydroxyphenyl)propanes", "endocrine-disruptors", "trifluoromethyl-compounds", "plasticizers"] topic_path: "general/2-2-bis-4-hydroxyphenyl-propanes" source: "https://en.wikipedia.org/wiki/Bisphenol_AF" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

|Watchedfields = changed |verifiedrevid = 461577920 |ImageFile=Bisphenol_AF.svg |ImageSize=200px |PIN=4,4′-(1,1,1,3,3,3-Hexafluoropropane-2,2-diyl)diphenol |OtherNames=Biphenol AF; Hexafluorobisphenol A; Hexafluorodiphenylolpropane; Bisphenol A hexafluoride; 4,4'-(Hexafluoroisopropylidene)diphenol; Hexafluoroacetone bisphenol A; 2,2-Bis(4-hydroxyphenyl)hexafluoropropane |Section1={{Chembox Identifiers |Abbreviations = BPAF |CASNo_Ref = |CASNo=1478-61-1 |UNII_Ref = |UNII = OH7IX8A37J |PubChem=73864 |SMILES=C1=CC(=CC=C1C(C2=CC=C(C=C2)O)(C(F)(F)F)C(F)(F)F)O |ChemSpiderID_Ref = |ChemSpiderID = 66498 |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 |InChIKey = ZFVMWEVVKGLCIJ-UHFFFAOYAS |StdInChI_Ref = |StdInChI = 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 |StdInChIKey_Ref = |StdInChIKey = ZFVMWEVVKGLCIJ-UHFFFAOYSA-N |Section2={{Chembox Properties |C=15 | H=10 | F=6 | O=2 |MeltingPt=162 °C

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.

Biological and Chemical Action

Bisphenol AF is an endocrine disrupting chemical. 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.

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

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.

References

References

  1. (2011). "HF-mediated equilibrium between fluorinated ketones and the corresponding α-fluoroalcohols". Tetrahedron.
  2. (September 2019). "Assessment of the endocrine disrupting properties of Bisphenol AF according to the EU criteria and ECHA/EFSA guidance". EFSA Journal.
  3. "Janet Raloff: Another plastics ingredient raises safety concerns, Science News, June 5th, 2010; Vol.177 #12 (p. 14)".
  4. (2011). "HF-mediated equilibrium between fluorinated ketones and the corresponding α-fluoroalcohols". Tetrahedron.
  5. "Bisphenol AF". National Library of Medicine.

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2,2-bis(4-hydroxyphenyl)propanesendocrine-disruptorstrifluoromethyl-compoundsplasticizers