Hexafluoro-2-propanol

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. (CF3)2CHOH is classified as a hard Lewis acid and its acceptor properties are discussed in the ECW model. Its relative acceptor strength toward a series of bases, versus other Lewis acids, can be illustrated by C-B plots.[1][2] Dual XH–π interaction of HFIP with arenes has been found (benzene/HFIP, 7.22 kcal/mol)[3] even stronger than the hydrogen bond in a water dimer (5-6 kcal/mol). Hexafluoro-2-propanol is transparent to UV light with high density, low viscosity and low refractive index.

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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.011.873
RTECS number
  • UB6450000
UNII
  • InChI=1S/C3H2F6O/c4-1(5)2(6,10)3(7,8)9/h1,10H Y
    Key: NMFQPFSIPWZZMR-UHFFFAOYSA-N Y
  • InChI=1S/C3H2F6O/c4-2(5,6)1(10)3(7,8)9/h1,10H
    Key: BYEAHWXPCBROCE-UHFFFAOYSA-N
  • C(C(F)(F)F)(C(F)(F)F)O
Properties
C3H2F6O
Molar mass 168.038 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
GHS labelling:
Danger
H314, H361fd, H373
P201, P280, P303+P361+P353, P305+P351+P338+P310, P308+P313
NFPA 704 (fire diamond)
3
0
0
Flash point > 100 °C (212 °F; 373 K)
Safety data sheet (SDS) External MSDS
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 YN ?)
Infobox references

Production and uses

Hexafluoro-propan-2-ol is prepared from hexafluoropropylene through hexafluoroacetone, which is then hydrogenated.[4]

(CF3)2CO + H2 → (CF3)2CHOH

Hexafluoro-propan-2-ol is a speciality solvent for some polar polymers[5] and organic synthesis.[6][7][8] 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.[9] Recent studies[10] showed an ability of HFIP to activate allylic alcohols, stabilise an allylic cation, and further functionalize to allylic sulphides and sulfones.

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.[11][12]

Safety

Hexafluoro-2-propanol is a volatile, corrosive liquid that can cause severe burns and respiratory problems. Animal experiments show possible adverse effects on fertility,[13] placing HFIP as a reproductive toxicity category 2 material.[14]

Environment

PMT/vPvM substances are very persistent in the environment and very mobile in the aquatic environment (vPvM); or, substances that are persistent in the environment, mobile in the aquatic environment and toxic (PMT). According to REACH, HFIP meets the PMT/vPvM criteria, but as of May 2017 is considered exempt from the PMT/vPvM assessment as HFIP belongs to Category 4: Exempt PMT/vPvM substances.[15] HFIP also belongs to per- and polyfluorinated alkyl substances (PFAS). There is no precisely clear definition of what constitutes a PFAS substance given the inclusion of partially fluorinated substances, polymers, and ill-defined reaction products on these various lists.[16]

References
  1. Laurence, C. and Gal, J-F. Lewis Basicity and Affinity Scales, Data and Measurement, (Wiley 2010) pp 50-51 ISBN 978-0-470-74957-9
  2. Cramer, R. E., and 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 54 612-613, Improved E&C parameters are listed in ECW model. The plots shown in this paper used older parameters.
  3. Lu, Le; Hua, Ruimao (28 July 2021). "Dual XH–π Interaction of Hexafluoroisopropanol with Arenes". Molecules. 26 (15): 4558. doi:10.3390/molecules26154558. PMC 8347120. PMID 34361719.
  4. 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
  5. Lu, Le; Hua, Ruimao (20 May 2021). "A Monomer‐Polymer‐Monomer (MPM) Organic Synthesis Strategy: Synthesis and Application of Polybenzofuran for Functionalizing Benzene Ring of Benzofuran". Asian Journal of Organic Chemistry: ajoc.202100208. doi:10.1002/ajoc.202100208.
  6. Lu, Le; Liu, Huixin; Hua, Ruimao (June 2018). "HNO3/HFIP: A Nitrating System for Arenes with Direct Observation of π-Complex Intermediates". Organic Letters. 20 (11): 3197–3201. doi:10.1021/acs.orglett.8b01028.
  7. 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.
  8. Shuklov, Ivan A.; Dubrovina, Natalia V.; Börner, Armin (2007). "Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis". Synthesis. 2007 (19): 2925–2943. doi:10.1055/s-2007-983902.
  9. 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. PMID 21639339.
  10. Lu, Maojian; Zhang, Rong-Jin; Zhu, Can-Ming; Xiao, Yonghong; Chen, Jian-Rui; Zhao, Lei-Min; Tong, Qing-Xiao; Zhong, Jian-Ji (October 2022). "HFIP-Induced Allylation Reaction of Tertiary Allylic Alcohols with Thiols or Sulfonyl Hydrazines to Access Allylic Organosulfurs". Synlett. 33 (17): 1745–1750. doi:10.1055/a-1915-8309. ISSN 0936-5214.
  11. Baxter Healthcare Corporation (June 2017). "SEVOFLURANE- sevoflurane liquid DESCRIPTION". DailyMed. Retrieved 12 March 2021.
  12. "PubChem Compound Summary for CID 5206, Sevoflurane". PubChem. 2021. Retrieved 12 March 2021.
  13. "1,1,1,3,3,3-hexafluoropropan-2-ol Toxicity to Reproduction". ECHA. Retrieved 26 March 2021.
  14. "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.
  15. 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.
  16. United States Environmental Protection Agency. "PFAS Master List of PFAS Substances (Version 2)". comptox.epa.gov/. Retrieved 12 March 2021.

Sources
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