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
Hexafluoroisopropanol 3D.png
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 Edit this at Wikidata
RTECS number
  • UB6450000
UNII
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
Safety data sheet External MSDS
GHS pictograms GHS05: Corrosive GHS08: Health hazard
GHS Signal word Danger
GHS hazard statements
 H314, H361fd, H373
P201, P280, P303+361+353, P305+351+338+310, P308+313
NFPA 704 (fire diamond)
3
0
0
Flash point > 100 °C (212 °F; 373 K)
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 [77 °F], 100 kPa).
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Infobox references

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.

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]

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.[10][11]

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,[12] placing HFIP as a reproductive toxicity category 2 material.[13]

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.[14] 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.[15] As a volatile and fluorinated substance, hexafluoroisopropanol has a potential to affect global warming.

References[]

  1. ^ Laurence, C. and Gal, J-F. Lewis Basicity and Affinity Scales, Data and Measurement, (Wiley 2010) pp 50-51 IBSN 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.
  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. ^ Baxter Healthcare Corporation (June 2017). "SEVOFLURANE- sevoflurane liquid DESCRIPTION". DailyMed. Retrieved 12 March 2021.
  11. ^ "PubChem Compound Summary for CID 5206, Sevoflurane". PubChem. 2021. Retrieved 12 March 2021.
  12. ^ "1,1,1,3,3,3-hexafluoropropan-2-ol Toxicity to Reproduction". ECHA. Retrieved 26 March 2021.
  13. ^ "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.
  14. ^ 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.
  15. ^ 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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