Uses
2-(4-aminobenzene)-1,1,1,3,3,3-hexafluoro-2-propanol can be used to prepare bisphenol AF. Bisphenol AF (hexafluorobisphenol A: 2,2-bis-(4-hydroxyphenyl)hexafluoropropane) is mainly used as a vulcanization accelerator for fluororubber.
Synthesis
To a xylene solution of aniline (7, 21.47 mmol) and p-toluenesulfonic acid (pTSA, 1.28 mmol) was added hexafluoroacetone trihydrate (8, 64.42 mmol) and the reaction mixture was heated to reflux for 5 hours. Upon completion of the reaction, it was cooled to room temperature to allow the product 4-(hexafluoro-2-hydroxyisopropyl)aniline (9) to crystallize and precipitate, which was collected by filtration and used directly in the next step of the reaction.
References
[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 6, p. 1638 - 1642
[2] European Journal of Medicinal Chemistry, 2016, vol. 122, p. 744 - 755
[3] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1990, vol. 39, # 2.2, p. 323 - 328
[4] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1990, # 2, p. 383 - 389
