Hexafluoro-2-propanol

Last updated
1,1,1,3,3,3-Hexafluoro-2-propanol
Hexafluoroisopropanol.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
RTECS number
  • UB6450000
UNII
  • InChI=1S/C3H2F6O/c4-1(5)2(6,10)3(7,8)9/h1,10H Yes check.svgY
    Key: NMFQPFSIPWZZMR-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceColorless 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:
GHS-pictogram-acid.svg GHS-pictogram-silhouette.svg
Danger
H314, H361fd, H373
P201, P280, P303+P361+P353, P305+P351+P338+P310, P308+P313
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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]

Hexafluoro-propan-2-ol has also been evaluated as a solvent for electrolysis. [7]

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. [8] [9]

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, [10] placing HFIP as a reproductive toxicity category 2 material. [11]

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. [12] HFIP also belongs to per- and polyfluorinated alkyl substances (PFAS). [13]

Related Research Articles

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In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl functional group bound to a saturated carbon atom. Alcohols range from the simple, like methanol and ethanol, to complex, like sugars and cholesterol. The presence of an OH group strongly modifies the properties of hydrocarbons, conferring hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur.

<span class="mw-page-title-main">Solvent</span> Substance dissolving a solute resulting in a solution

A solvent is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for polar molecules, and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within the cell.

Acetonitrile, often abbreviated MeCN, is the chemical compound with the formula CH3CN and structure H3C−C≡N. This colourless liquid is the simplest organic nitrile. It is produced mainly as a byproduct of acrylonitrile manufacture. It is used as a polar aprotic solvent in organic synthesis and in the purification of butadiene. The N≡C−C skeleton is linear with a short C≡N distance of 1.16 Å.

<span class="mw-page-title-main">Lithium aluminium hydride</span> Chemical compound

Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula Li[AlH4] or LiAlH4. It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters, carboxylic acids, and amides. The solid is dangerously reactive toward water, releasing gaseous hydrogen (H2). Some related derivatives have been discussed for hydrogen storage.

In chemistry, a dehydration reaction is a chemical reaction that involves the loss of water from the reacting molecule or ion. Dehydration reactions are common processes, the reverse of a hydration reaction.

<span class="mw-page-title-main">2,2,2-Trifluoroethanol</span> Chemical compound

2,2,2-Trifluoroethanol is the organic compound with the formula CF3CH2OH. Also known as TFE or trifluoroethyl alcohol, this colourless, water-miscible liquid has a smell reminiscent of ethanol. Due to the electronegativity of the trifluoromethyl group, this alcohol exhibits a stronger acidic character compared to ethanol.

<span class="mw-page-title-main">Hydroxymethylfurfural</span> Chemical compound

Hydroxymethylfurfural (HMF), also known as 5-(hydroxymethyl)furfural, is an organic compound formed by the dehydration of reducing sugars. It is a white low-melting solid which is highly soluble in both water and organic solvents. The molecule consists of a furan ring, containing both aldehyde and alcohol functional groups.

<span class="mw-page-title-main">Isobutanol</span> Chemical compound

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

<span class="mw-page-title-main">Propyl acetate</span> Chemical compound

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<span class="mw-page-title-main">Hexafluoroacetone</span> Chemical compound

Hexafluoroacetone (HFA) is a chemical compound with the formula (CF3)2CO. It is structurally similar to acetone; however, its reactivity is markedly different. It a colourless, hygroscopic, nonflammable, highly reactive gas characterized by a musty odour. The most common form of this substance is hexafluoroacetone sesquihydrate (1.5 H2O), which is a hemihydrate of hexafluoropropane-2,2-diol (F
3C)
2C(OH)
2, a geminal diol.

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References

  1. 1 2 3 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. 1 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.

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