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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
Names
Preferred IUPAC name 1,1,1,3,3,3-Hexafluoropropan-2-ol
Other names Hexafluoroisopropanol,
Hexafluoroisopropyl alcohol,
HFIP
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.011.873 Edit this at Wikidata
PubChem CID
RTECS number
  • UB6450000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H2F6O/c4-1(5)2(6,10)3(7,8)9/h1,10HKey: NMFQPFSIPWZZMR-UHFFFAOYSA-N
  • InChI=1S/C3H2F6O/c4-2(5,6)1(10)3(7,8)9/h1,10HKey: BYEAHWXPCBROCE-UHFFFAOYSA-N
SMILES
  • C(C(F)(F)F)(C(F)(F)F)O
Properties
Chemical formula C3H2F6O
Molar mass 168.038 g·mol
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
GHS labelling:
Pictograms GHS05: Corrosive GHS08: Health hazard
Signal word Danger
Hazard statements H314, H361fd, H373
Precautionary statements P201, P280, P303+P361+P353, P305+P351+P338+P310, P308+P313
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3 0 0
Flash point > 100 °C (212 °F; 373 K)
Safety data sheet (SDS) External MSDS
Related compounds
Related Organofluorides;
alcohols 		Hexafluoroacetone;
Isopropyl alcohol, 2,2,2-Trifluoroethanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Hexafluoroisopropanol, commonly abbreviated HFIP, is the organic compound with the formula (CF3)2CHOH. This fluoroalcohol finds use as solvent in organic chemistry. Hexafluoro-2-propanol is transparent to UV light with high density, low viscosity and low refractive index. It is a colorless, volatile liquid with a pungent odor.

Production

Hexafluoro-propan-2-ol is prepared from hexafluoropropylene through hexafluoroacetone, which is then hydrogenated.

(CF3)2CO + H2 → (CF3)2CHOH

Solvent properties

As a solvent, hexafluoro-2-propanol is polar and exhibits strong hydrogen bonding properties. Testament to the strength of its hydrogen-bonding tendency is the fact that its 1:1 complex with THF distills near 100 °C. It has a relatively high dielectric constant of 16.7. It is also relatively acidic, with a pKa of 9.3, comparable to that for phenol. It is classified as a hard Lewis acid and its acceptor properties are discussed in the ECW model.

Hexafluoro-propan-2-ol is a speciality solvent for organic synthesis, particularly for reactions involving oxidations and strong electrophiles. For example, HFIP enhances the reactivity of hydrogen peroxide as applied to Baeyer-Villiger oxidation of cyclic ketones. In another illustration of its use, HFIP is used as the solvent for Lewis-acid catalyzed ring opening of epoxides.

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.

Hexafluoro-propan-2-ol has also been evaluated as a solvent for electrolysis.

Medicine

It is both the precursor and the chief metabolite of the inhalation anesthetic sevoflurane. Sevoflurane gets metabolized within the body into HFIP and formaldehyde. HFIP is inactive, non-genotoxic and once formed, is rapidly conjugated with glucuronic acid and eliminated as a urinary metabolite.

Safety

Toxicity

Hexafluoro-2-propanol has very low acute toxicity, hence its use as a precursor to anesthetics. Although it has low acute toxicity, it is a strong irritant to skin and eyes. Animal experiments show possible adverse effects on fertility, placing HFIP as a reproductive toxicity category 2 material.

Environment and toxicity

HFIP is a specialty chemical that is produced in small quantities, thus it is not of significant environmental concern. Its environmental implications have been assessed. HFIP also belongs to per- and polyfluorinated alkyl substances (PFAS).

References

  1. ^ Colomer, Ignacio; Chamberlain, Anna E. R.; Haughey, Maxwell B.; Donohoe, Timothy J. (2017). "Hexafluoroisopropanol as a Highly Versatile Solvent". Nature Reviews Chemistry. 1 (11). doi:10.1038/s41570-017-0088.
  2. ^ 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
  3. Laurence, C.; Gal, J-F. (2010). Lewis Basicity and Affinity Scales, Data and Measurement. Wiley. p. 50-51. ISBN 978-0-470-74957-9.{{cite book}}: CS1 maint: multiple names: authors list (link)
  4. Cramer, R. E.; Bopp, T. T. (1977). "Great E and C Plot. Graphical Display of the Enthalpies of Adduct Formation for Lewis Acids and Bases". Journal of Chemical Education. 54 (10): 612-613. doi:10.1021/ed054p612.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. Travis W.Shaw, Julia A.Kalow, Abigail G.Doyle (2012). "Fluoride Ring-Opening Kinetic Resolution of Terminal Epoxides: Preparation of (S)-2-Fluoro-1-phenylethanol". Organic Syntheses. 89: 9. doi:10.15227/orgsyn.089.0009.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  6. 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 (7): 1320–1325. doi:10.1021/ac960916h. PMID 21639339.
  7. Ramos-Villaseñor, José Manuel; Rodríguez-Cárdenas, Esdrey; Barrera Díaz, Carlos E.; Frontana-Uribe, Bernardo A. (2020). "Review—Use of 1,1,1,3,3,3–hexafluoro–2–propanol (HFIP) Co-Solvent Mixtures in Organic Electrosynthesis". Journal of the Electrochemical Society. 167 (15): 155509. doi:10.1149/1945-7111/abb83c. S2CID 224972047.
  8. Baxter Healthcare Corporation (June 2017). "SEVOFLURANE- sevoflurane liquid DESCRIPTION". DailyMed. Retrieved 12 March 2021.
  9. "PubChem Compound Summary for CID 5206, Sevoflurane". PubChem. 2021. Retrieved 12 March 2021.
  10. "1,1,1,3,3,3-hexafluoropropan-2-ol Toxicity to Reproduction". ECHA. Retrieved 26 March 2021.
  11. "REGULATION (EC) No 1272/2008 OF THE EUROPEAN PARLIAMENT AND OF THE COUNCIL of 16 December 2008 on classification, labelling and packaging of substances and mixtures, amending and repealing Directives 67/548/EEC and 1999/45/EC, and amending Regulation (EC) No 1907/2006". Official Journal of the European Union: 109. 31 December 2008. Retrieved 26 March 2021.
  12. Arp, Hans Peter H.; Hale, Sarah E. (November 2019). "REACH: Improvement of guidance and methods for the identification and assessment of PMT/vPvM substances". umweltbundesamt.de. Umweltbundesamt. Retrieved 12 March 2021.
  13. United States Environmental Protection Agency. "PFAS Master List of PFAS Substances (Version 2)". comptox.epa.gov/. Retrieved 12 March 2021.

Sources

External links

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