|Jmol-3D images||Image 1|
|Molar mass||168.04 g mol−1|
|Melting point||−3.3 °C (26.1 °F; 269.8 K)|
|Boiling point||58.2 °C (136.8 °F; 331.3 K)|
|Solubility in water||Miscible|
|Vapor pressure||16 kPa at 20 °C|
|Viscosity||1.65 cP at 20 °C|
|R-phrases||R20/22, R34, R41|
|S-phrases||S26, S36/37/39, S45|
|Main hazards||Corrosive (C)|
|Flash point||>100 °C|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
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.
Production and uses
- (CF3)2CO + H2 → (CF3)2CHOH
Hexafluoro-2-propanol is a speciality solvent for some polar polymers and organic synthesis. 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.
Hexafluoro-2-propanol is a volatile, corrosive gas which can cause severe respiratory problems.
- Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick “Fluorine Compounds, Organic” in Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, 2007. doi:10.1002/14356007.a11_349
- Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. (2004). "Fluorinated Alcohols: A New Medium for Selective and Clean Reaction". Synlett (1): 18–29.
- Shuklov, Ivan A. ; Dubrovina, Natalia V.; Börner, Armin (2007). "Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis". Synthesis: 2925–2943. doi:10.1055/s-2007-983902.
- Apffel, A.; Chakel, J.A.; Fischer, S.; Lichtenwalter, K.; Hancock, W.S. (1997). "Analysis of oligonucleotides by HPLC-electrospray ionization mass spectrometry". Anal. Chem 69: 1320–1325.
- Radlick, Phillip C (1982-02-02). "Methods of synthesizing hexafluoroisopropanol from impure mixtures and synthesis of a fluoromethyl ether therefrom". United States Patent 4,314,087. Retrieved 2006-10-18.
- Cheminal, Bernard; H. Mathais and M. Thomarat (1987-03-03). "Process for the synthesis of 2,2,2-trifluoroethanol and 1,1,1,3,3,3-hexafluoroisopropanol". United States Patent 4,647,706. Retrieved 2006-10-18.