Chemistry:Hexafluoro-2-propanol
Names | |
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Preferred IUPAC name
1,1,1,3,3,3-Hexafluoropropan-2-ol | |
Other names
Hexafluoroisopropanol,
Hexafluoroisopropyl alcohol, HFIP | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
PubChem CID
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RTECS number |
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UNII | |
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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 | |
GHS Signal word | DANGER |
H314, H361fd, H373 | |
P201, P280, P303+361+353, P305+351+338+310, P308+313 | |
NFPA 704 (fire diamond) | |
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). | |
verify (what is ?) | |
Infobox references | |
Hexafluoroisopropanol, commonly abbreviated HFIP, is the organic compound with the formula (CF3)2CHOH. This fluoroalcohol finds use as solvent in organic chemistry.[1] 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.[2]
- (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.[1] It is classified as a hard Lewis acid and its acceptor properties are discussed in the ECW model.[3][4]
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.[1] In another illustration of its use, HFIP is used as the solvent for Lewis-acid catalyzed ring opening of epoxides.[5]
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.[6] Recent studies[7] showed an ability of HFIP to activate allylic alcohols, stabilise an allylic cation, and further functionalize to allylic sulphides and sulfones.
Hexafluoro-propan-2-ol is a speciality solvent for some polar polymers.[8] It solubilizes polymers that are insoluble in common organic solvents, such as: polyamides, polyacrylonitriles, polyacetals, polyesters (e.g. polyglycolide), and polyketones. It has also been evaluated as a solvent for electrolysis.[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
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.[2] Animal experiments show possible adverse effects on fertility,[12] placing HFIP as a reproductive toxicity category 2 material.[13]
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.[14] HFIP also belongs to per- and polyfluorinated alkyl substances (PFAS).[15]
References
- ↑ 1.0 1.1 1.2 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. https://ora.ox.ac.uk/objects/uuid:72dc250a-656e-4367-827d-17835acc28ba.
- ↑ 2.0 2.1 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
- ↑ Laurence, C.; Gal, J-F. (2010). Lewis Basicity and Affinity Scales, Data and Measurement. Wiley. p. 50-51. ISBN 978-0-470-74957-9.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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" (in en). Synlett 33 (17): 1745–1750. doi:10.1055/a-1915-8309. ISSN 0936-5214. http://www.thieme-connect.de/DOI/DOI?10.1055/a-1915-8309.
- ↑ 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 10 (8): 2137–2142. doi:10.1002/ajoc.202100208.
- ↑ 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.
- ↑ Baxter Healthcare Corporation (June 2017). "SEVOFLURANE- sevoflurane liquid DESCRIPTION". https://www.dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=ea8bf997-2c71-4014-b18d-4f7ab45dfa19&type=display.
- ↑ "PubChem Compound Summary for CID 5206, Sevoflurane". 2021. https://pubchem.ncbi.nlm.nih.gov/compound/Sevoflurane.
- ↑ "1,1,1,3,3,3-hexafluoropropan-2-ol Toxicity to Reproduction". https://echa.europa.eu/registration-dossier/-/registered-dossier/21690/7/9/2.
- ↑ "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. https://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:32008R1272&from=EN. Retrieved 26 March 2021.
- ↑ 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. https://www.umweltbundesamt.de/en/publikationen/reach-improvement-of-guidance-methods-for-the.
- ↑ United States Environmental Protection Agency. "PFAS Master List of PFAS Substances (Version 2)". https://comptox.epa.gov/dashboard/chemical_lists/pfasmaster.
Sources
- Radlick, Phillip C (1982-02-02). "Methods of synthesizing hexafluoroisopropanol from impure mixtures and synthesis of a fluoromethyl ether therefrom". United States Patent 4,314,087. http://www.freepatentsonline.com/4314087.html. Retrieved 2006-10-18.
- Cheminal, Bernard; H. Mathais (1987-03-03). "Process for the synthesis of 2,2,2-trifluoroethanol and 1,1,1,3,3,3-hexafluoroisopropanol". United States Patent 4,647,706. http://www.freepatentsonline.com/4647706.html. Retrieved 2006-10-18.
External links
Original source: https://en.wikipedia.org/wiki/Hexafluoro-2-propanol.
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