Hexafluoroisopropyl alcohol

Hexafluoroisopropanol, commonly abbreviated HFIP, is the organic compound with the formula (CF₃)₂CHOH. This fluoroalcohol finds use as solvent in organic chemistry. Hexafluoro-2-propanol is transparent to UV light with high density, low viscosity and low refractive index

Hexafluoroisopropanol Production

Hexafluoro-propan-2-ol is prepared from hexafluoropropylene through hexafluoroacetone, which is then hydrogenated.

(CF₃)₂CO + H₂ → (CF₃)₂CHOH

Solvent Properties

Hexafluoroisopropyl alcohol as a solvent, hexafluoro-2-propanol is polar and exhibits strong hydrogen bonding properties. Testament to the strength of its hydrogen-bonding tendency is the fact that its 1:1 complex with THF distills near 100 °C. It has a relatively high dielectric constant of 16.7. It is also relatively acidic, with a pKa of 9.3, comparable to that for phenol.

It is classified as a hard Lewis acid and its acceptor properties are discussed in the ECW model.

Hexafluoro-propan-2-ol is a speciality solvent for organic synthesis, particularly for reactions involving oxidations and strong electrophiles. For example, HFIP enhances the reactivity of hydrogen peroxide as applied to Baeyer-Villiger oxidation of cyclic ketones.

In another illustration of its use, HFIP is used as the solvent for Lewis-acid catalyzed ring opening of epoxides.