bisphenol AF
{{chembox
|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 = {{cascite|correct|??}}
|CASNo=1478-61-1
|UNII_Ref = {{fdacite|correct|FDA}}
|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 = {{chemspidercite|correct|chemspider}}
|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 = {{stdinchicite|correct|chemspider}}
|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 = {{stdinchicite|correct|chemspider}}
|StdInChIKey = ZFVMWEVVKGLCIJ-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
|C=15 | H=10 | F=6 | O=2
}}
}}
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
{{see|endocrine disruptor}}
Bisphenol AF is an endocrine disrupting chemical.{{cite journal |last1=Escrivá |first1=Laura |last2=Hanberg |first2=Annika |last3=Zilliacus |first3=Johanna |last4=Beronius |first4=Anna |title=Assessment of the endocrine disrupting properties of Bisphenol AF according to the EU criteria and ECHA/EFSA guidance |journal=EFSA Journal |date=September 2019 |volume=17 |issue=EU‐FORA: Series 2 |pages=e170914 |doi=10.2903/j.efsa.2019.e170914|pmid=32626472 |pmc=7015508 }}
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.{{Cite web |url=http://www.sciencenews.org/view/generic/id/59113 |title=Janet Raloff: Another plastics ingredient raises safety concerns, Science News, June 5th, 2010; Vol.177 #12 (p. 14) |access-date=2010-06-11 |archive-date=2012-09-27 |archive-url=https://web.archive.org/web/20120927005453/http://www.sciencenews.org/view/generic/id/59113 |url-status=dead }}
The chemical shifts in 1H, 13C and 19F NMR spectroscopy are given in the literature.{{Cite journal|last1=Hayasaka|first1=Tatsuya|last2=Katsuhara|first2=Yutaka|last3=Kume|first3=Takashi|last4=Yamazaki|first4=Takashi|title=HF-mediated equilibrium between fluorinated ketones and the corresponding α-fluoroalcohols|journal=Tetrahedron|volume=67|issue=12|pages=2215–2219|doi=10.1016/j.tet.2011.01.087|year=2011}}
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.{{cite web |title=Bisphenol AF |url=https://pubchem.ncbi.nlm.nih.gov/compound/Bisphenol-AF |website=PubChem |publisher=National Library of Medicine |access-date=20 January 2021}}
See also
References
{{Reflist}}
{{Estrogen-related receptor modulators}}
Category:2,2-Bis(4-hydroxyphenyl)propanes