Hexafluoro-2-propanol
From Wikipedia, the free encyclopedia
| 1,1,1,3,3,3-Hexafluoro-2-propanol | |
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1,1,1,3,3,3-Hexafluoro
-2-propanol |
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other names
Hexafluoroisopropanol,
Hexafluoroisopropyl alcohol, HFIP |
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| Identifiers | |
| CAS number | 920-66-1  |
| PubChem | 13529 |
| RTECS number | UB6450000 |
| SMILES |
C(F)(F)(F)C(O)C(F)(F)(F)
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| 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
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| Flash point | >373°C |
| Related compounds | |
| Related organofluorides | Hexafluoro-2-propanone |
| (what is this?) (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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.
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[edit] 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 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. 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.
[edit] Safety
Hexafluoro-2-propanol is volatile and corrosive. Its vapors therefore can cause severe respiratory problems.
[edit] References
[edit] 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.
[edit] 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.
