Hexafluoro-2-propanol

1,1,1,3,3,3-Hexafluoro-2-propanol
Names
IUPAC names
1,1,1,3,3,3-Hexafluoro
-2-propanol
Other names
Hexafluoroisopropanol,
Hexafluoroisopropyl alcohol,
HFIP
Identifiers
920-66-1 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:63104 N
ChemSpider 10606755 YesY
ECHA InfoCard 100.011.873
PubChem 13529
RTECS number UB6450000
Properties
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)
Miscible
Vapor pressure 16 kPa at 20 °C
Viscosity 1.65 cP at 20 °C
Hazards
Main hazards Corrosive (C)
Safety data sheet External MSDS
R-phrases R20/22, R34, R41
S-phrases S26, S36/37/39, S45
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
0
3
0
Flash point > 100 °C (212 °F; 373 K)
Related compounds
Hexafluoroacetone;
Isopropyl alcohol, 2,2,2-Trifluoroethanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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

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

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

Safety

Hexafluoro-2-propanol is a volatile, corrosive liquid that can cause severe burns and respiratory problems.[5]

References

Notes

  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. doi:10.1055/s-2003-44973.
  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. doi:10.1021/ac960916h.
  5. ↑ "HFIP MSDS". Fisher Scientific. Retrieved 2014-08-18.

Sources

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