Description
Production
Hexafluoro-propan-2-ol is prepared from hexafluoropropylene through hexafluoroacetone, which is then hydrogenated.
- (CF3)2CO + H2 → (CF3)2CHOH
Density (D) 1,62 g/cm³
Boiling point (bp) 59 °C
Flash point (flp) >100 °C
Melting point (mp) -2 °C
Molar mass: 168.05 g/mol
Formula: C3H2F6O
Density: 1.6 g/cm³
Solubility in water: Miscible
Viscosity: 1.65 cP at 20 °C
CAS No: 920-66-1
CHEBI: 63104
ChemSpider: 10606755
ECHA InfoCard: 100.011.873
PubChem CID: 13529
RTECS number: UB6450000
UNII: 3D632GYQ50 check
Solvent properties
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 8.3, 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.
Synonym(s):
HFP, Hexafluoroisopropanol, 1,1,1,3,3,3-Hexafluoropropan-2-ol, Hexafluoroisopropanol,
Hexafluoroisopropyl alcohol, HFIP,
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