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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 SMILES FC(F)(F)C(F)(O)C(F)F InChI InChI=1S/C3H2F6O/c4-1(5)2(6,10)3(7,8)9/h1,10H Y Key: NMFQPFSIPWZZMR-UHFFFAOYSA-N Y InChI=1/C3H2F6O/c4-1(5)2(6,10)3(7,8)9/h1,10H Key: NMFQPFSIPWZZMR-UHFFFAOYAZ 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 NFPA 704 0 3 0 Flash point >100°C (373 K) Related compounds Related organofluorides Hexafluoro-2-propanone  Y(what is this?)  (verify) 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 1 Production and uses 2 Safety 3 References 3.1 Notes 3.2 Sources // 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 therefore can cause severe respiratory problems. References Notes ^ 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 ^ Review: Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. Fluorinated Alcohols: A New Medium for Selective and Clean Reaction. Synthesis, 2004,(1), pp. 18-29. ^ Review: Shuklov, Ivan A. ; Dubrovina, Natalia V.; Börner, Armin Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis, Synthesis 2007, pp. 2925-2943 ^ 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 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. http://www.freepatentsonline.com/4314087.html. 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. http://www.freepatentsonline.com/4647706.html. Retrieved 2006-10-18.  "Hexafluoroisopropanol datasheet". DuPont. http://www.dupont.com/polymerspecialties/HFIP.html. Retrieved 2006-10-18.