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Published TCIMAIL newest issue No.197

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Fluorinated Alcohol with Unique Properties: HFIP

H0424: Hexafuoroisopropyl Alcohol (= HFIP)

H0424

Features

• Highly polar, thermally stable, UV transparent
• Miscible with water and polar organic solvents
• Low nucleophilicity
• Strong solvating power through hydrogen bonds

Physical Properties (from literature)

• bp: 58.6°C
• mp: -4°C
• Density: 1.605
• pK_a: 9.3
• Polarity (E^N_T): 1.068 (vs E^N_T(Me₄Si) = 0, E^N_T(water) = 1)
• Nucleophilicity (N): -4.23 (vs N(EtOH) = 0)
• Hydrogen bond donor power (α): 1.96 (vs α(EtOH) = 0)
• Hydrogen bond acceptor power (β): 0 (vs β(EtOH) = 0.77)

Reviews

Applications

1) Deprotecting agent for nucleoside and nucleotide synthesis

- N. J. Leonard, Neelima, Tetrahedron Lett. 1995, 36, 7833.

2) Additive for oligonucleotides analysis by HPLC/ESI-MS

- A. Apffel, J. A. Chakel, S. Fischer, K. Lichtenwalter, W. S. Hancock, Anal. Chem. 1997, 69, 1320.
- R. Erb, H. Oberacher, Electrophoresis 2014, 35, 1226.

3) Solvent for olefin epoxidation by hydrogen peroxide

- M. C. A. van Vliet, I. W. C. E. Arends, R. A. Sheldon, Synlett 2001, 2, 248.
- A. Berkessel, J. A. Adrio, J. Am. Chem. Soc. 2006, 128, 13412.

4) Solvent for catalytic oxidation

- J.-E. Bäckvall, A. Berkessel, Modern Oxidation Methods, 2nd ed., ed. by J.-E. Bäckvall, Wiley-VCH, Weinheim, Germany, 2010, Chap. 4, pp. 117-145.

5) Solvent for metal-catalyzed cyclization

- A. Saito, A. Kanno, Y. Hanzawa, Angew. Chem. Int. Ed. 2007, 46, 3931.
- M. Yokota, D. Fujita, J. Ichikawa, Org. Lett. 2007, 9, 4639.

6) Solvent for stabilizing radical cation

- L. Eberson, M. P. Hartshorn, O. Persson, F. Radner, Chem. Commun. 1996, 2105.
- Organofluorine Chemistry, ed. by K. Uneyama, John Wiley & Sons, Florida, 2008, pp. 180-184.

7) Solvent for radical polymerization

- K. Yamada, T. Nakano, Y. Okamoto, J. Polym. Sci. A Polym. 1999, 37, 2677.
- D. Wan, K. Satoh, M. Kamigaito, Y. Okamoto, Macromolecules 2005, 38, 10397.

8) Solvent for MALDI-TOF-MS or GPC/SEC analysis of polymers

- A. J. Hoteling, T. H. Mourey, K. G. Owens, Anal. Chem. 2005, 77, 750.
- Encyclopedia of Chromatography, 2nd ed., ed. by J. Cazes, CRC Press, Florida, 2005, pp. 1305-1314.

9) Stabilizer for α-helical conformation in unfolded proteins and peptides

- N. Hirota, K. Mizuno, Y. Goto, Protein Sci. 1997, 6, 416.
- D.-P. Hong, M. Hoshino, R. Kuboi, Y. Goto, J. Am. Chem. Soc. 1999, 121, 8427.

Related Products

T0435: 2,2,2-Trifuoroethanol (= TFE)

T0431: Trifuoroacetic Acid (= TFA)

T1336: Trifluoroacetic Acid Sodium Salt

Related Product Categories

Nucleosides, Nucleotides, Oligonucleotides

Polymer/Macromolecule Reagents

Biostabilization Agents

The brochure is in the link below.

Fluorinated Alcohol with Unique Properties: HFIP (PDF file)