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Fluoroalcohol

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

Perfluoroalcohols

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

CF3OH → COF2 + HF

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. Fluorotelomer alcohols are precursors to perfluorocarboxylic acids. Pirkle's alcohol is used a chiral shift reagent in nuclear magnetic resonance spectroscopy.

References

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