Hexafluoro-2-propanol

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1,1,1,3,3,3-Hexafluoro-2-propanol
1,1,1,3,3,3-Hexafluoro-2-propanol
Hexafluoroisopropanol 3D.png
Identifiers
CAS number 920-66-1 YesY
PubChem 13529
ChemSpider 10606755 YesY
ChEBI CHEBI:63104 YesY
RTECS number UB6450000
Jmol-3D images Image 1
Properties
Molecular formula C3H2F6O
Molar mass 168.04 g mol−1
Appearance Colorless liquid
Density 1.596 g/mL
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
Hazards
MSDS External MSDS
R-phrases R20/22, R34, R41
S-phrases S26, S36/37/39, S45
Main hazards Corrosive (C)
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point >100 °C
Related compounds
Related Organofluorides Hexafluoroacetone
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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.

Production and uses[edit]

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]

Medicine[edit]

It is both the precursor and the chief metabolite of the inhalation anesthetic sevoflurane.

Safety[edit]

Hexafluoro-2-propanol is a volatile, corrosive gas which can cause severe respiratory problems.[citation needed]

References[edit]

Notes[edit]

  1. ^ 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
  2. ^ Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. (2004). "Fluorinated Alcohols: A New Medium for Selective and Clean Reaction". Synlett (1): 18–29. 
  3. ^ 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. 
  4. ^ 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. 

Sources[edit]