What is 1,1,1,3,3,3-Hexafluoro-2-propanol?

Dec 30,2019

1,1,1,3,3,3-Hexafluoro-2-propanol also known as hexafluoroisopropanol, commonly abbreviated HFIP, is the organic compound with the formula (CF3)2CHOH. This fluoroalcohol 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 [1].

1,1,1,3,3,3-Hexafluoro-2-propanol is an organofluorine compound formed by substitution of all the methyl protons in propan-2-ol by fluorine. It is a metabolite of inhalation anesthetic sevoflurane. It has a role as a drug metabolite. It is an organofluorine compound and a secondary alcohol. It derives from a propan-2-ol. 1,1,1,3,3,3-hexafluoro-2-propanol is a clear colorless oily liquid with an aromatic odor. (NTP, 1992) Combustible, may cause burns to skin, eyes and mucous membranes [2].

1,1,1,3,3,3-Hexafluoro-2-propanol is prepared from hexafluoropropylene through hexafluoroacetone, which is then hydrogenated [3].

(CF3)2CO + H2 → (CF3)2CHOH

1,1,1,3,3,3-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 [4].

1,1,1,3,3,3-Hexafluoro-2-propanol is both the precursor and the chief metabolite of the inhalation anesthetic sevoflurane.

1,1,1,3,3,3-Hexafluoro-2-propanol is a volatile, corrosive liquid that can cause severe burns and respiratory problems.

1,1,1,3,3,3-Hexafluoro-2-propanol is a polar solvent of high ionizing power and facilitates Friedel–Crafts-type reactions, using covalent reagents in the absence of a Lewis acid catalyst. 1,1,1,3,3,3-Hexafluoro-2-propanol clusters catalyzes the epoxidation of cyclooctene and 1-octene with hydrogen peroxide.

1,1,1,3,3,3-Hexafluoro-2-propanol was used for preparing hexafluoroalcohol-functionalized methacrylate polymers for lithographic/nanopatterning materials [5].

References

[1] https://en.wikipedia.org/wiki/Hexafluoro-2-propanol
[2] https://pubchem.ncbi.nlm.nih.gov/compound/1_1_1_3_3_3-Hexafluoro-2-propanol
[3] 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
[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] https://www.sigmaaldrich.com/catalog/product/aldrich/105228?lang=en&region=US

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