Hexafluoro-2-propanol
Chemical compound From Wikipedia, the free encyclopedia
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.
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| 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 | |
| ECHA InfoCard | 100.011.873 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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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 | |
| GHS labelling: | |
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| Danger | |
| H314, H361fd, H373 | |
| P201, P280, P303+P361+P353, P305+P351+P338+P310, P308+P313 | |
| NFPA 704 (fire diamond) | |
| 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).
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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]
References
External links
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