Hexafluoro-2-propanol

1,1,1,3,3,3-Hexafluoro-2-propanol
IUPAC name

1,1,1,3,3,3-Hexafluoro
-2-propanol
Other names

Hexafluoroisopropanol,
Hexafluoroisopropyl alcohol,
HFIP
Identifiers
CAS number 920-66-1 Y
PubChem 13529
ChemSpider 10606755 Y
RTECS number UB6450000
Jmol-3D images Image 1
Properties
Molecular formula C3H2F6O
Molar mass 168.05 g/mol
Appearance Colorless liquid
Density 1.596 g/ml, liquid
Melting point

−3.3 °C (269 K)
Boiling point

58.2 °C (331 K)
Solubility in water Miscible, 100 g/100 ml (25 °C)
Solubility in other solvents Miscible
Viscosity 1.65 cP at 20 °C
Hazards
MSDS External MSDS
R-phrases R20/22, R34, R41
S-phrases S26, S36/37/39, S45
Main hazards Corrosive (C)
NFPA 704
0
3
0
Flash point >100 °C (373 K)
Related compounds
Related organofluorides Hexafluoro-2-propanone
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Hexafluoroisopropanol, commonly abbreviated HFIP, is the organic compound with the formula (CF3)2CHOH. This fluorinated alcohol finds use as solvent and synthetic intermediate. It appears as a colorless, volatile liquid that is characterized by a strong, pungent odor. As a solvent hexafluoro-2-propanol is polar and exhibits strong hydrogen bonding properties enabling it to dissolve substances that serve as hydrogen-bond acceptors, such as amides and ethers. Hexafluoro-2-propanol is transparent to UV light with high density, low viscosity and low refractive index.

Contents

Production and uses

Hexafluoro-2-propanol is prepared from hexafluoropropylene via hexafluoroacetone, which is reduced by catalytic hydrogenation or by hydride reagents.[1]

(CF3)2CO + H2 → (CF3)2CHOH

Hexafluoro-2-propanol is a speciality solvent for some polar polymers and organic synthesis.[2][3] It is especially effective for solubilizing a wide range of polymers, including those that are not soluble in the most common organic solvents: such as polyamides, polyacrylonitriles, polyacetals, polyesters (e.g. polyglycolide), and polyketones. It has also found use in biochemistry to solubilize peptides and to monomerize β-sheet protein aggregates. Because of its acidity (pKa = 9.3), it can be used as acid in volatile buffers for ion pair HPLC - mass spectrometry of nucleic acids.[4]

It is the precursor to the inhalation anesthetic sevoflurane.

Safety

Hexafluoro-2-propanol is volatile and corrosive. Its vapors can cause severe respiratory problems and immediate, irreversible eye damage.

References

Notes

  1. ^ Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick “Fluorine Compounds, Organic” Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, 2007.doi:10.1002/14356007.a11_349
  2. ^ Review: Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. Fluorinated Alcohols: A New Medium for Selective and Clean Reaction. Synlett, 2004,(1), pp. 18-29.
  3. ^ Review: Shuklov, Ivan A. ; Dubrovina, Natalia V.; Börner, Armin Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis, Synthesis 2007, pp. 2925-2943
  4. ^ Apffel, A.; Chakel, J.A.; Fischer, S.; Lichtenwalter, K.; Hancock, W.S., Analysis of oligonucleotides by HPLC-electrospray ionization mass spectrometry. Anal. Chem, 1997,(69), pp. 1320-1325.

Sources