Fluoroalcohol Explained

Fluoroalcohols are organofluorine compounds consisting of an alcohol functional group with at least one C-F bond. These compounds often have distinctive solvent properties.^[1]

Perfluoroalcohols

Most primary and secondary perfluoroalcohols are unstable, for example trifluoromethanol eliminates hydrogen fluoride, forming carbonyl fluoride.^[2] This reaction is reversible.^[3]

Stable perfluorinated alcohols include nonafluoro-tert-butyl alcohol ((CF₃)₃COH) and pentafluorophenol (C₆F₅OH).

Partially fluorinated alcohols

Numerous partially fluorinated alcohols are known and have useable stabilities. Trifluoroethanol and hexafluoroisopropanol are used as solvents in research.^[4] Fluorotelomer alcohols are precursors to perfluorocarboxylic acids. Pirkle's alcohol is used a chiral shift reagent in nuclear magnetic resonance spectroscopy.

References

1. Synthesis. 2007. 2925–2943. 10.1055/s-2007-983902. Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis: Benefits from the Use of Fluorinated Alcohols in Homogeneous Catalysis . Ivan A. Shuklov . Natalia V. Dubrovina . Armin Börner.
2. Schneider. W. F.. Energetics and Mechanism of Decomposition of CF₃OH. J. Phys. Chem.. 1996. 100 . 15 . 6097–6103. 10.1021/jp952703m.
3. Perfluoroalcohols. Cheburkov, Yuri . Lillquist, Gerald J. . Journal of Fluorine Chemistry. 2002. 118. 1–2 . 123–126. 10.1016/S0022-1139(02)00204-X.
4. 10.1038/s41570-017-0088. Hexafluoroisopropanol as a Highly Versatile Solvent . 2017 . Colomer . Ignacio . Chamberlain . Anna E. R. . Haughey . Maxwell B. . Donohoe . Timothy J. . Nature Reviews Chemistry . 1 . 11 .