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Hexafluoro-2-propanol (erroneously called 鈥渉exafluoroisopropanol鈥�, abbreviated HFIP) is a low-boiling solvent used in a variety of chemical applications. It first appeared in the chemical literature in a 1960 Swiss patent to Soviet Union chemists Ivan L. Knunyants and M. P. Krasuskaya, who synthesized it by reducing hexafluoroacetone1 with sodium borohydride.
After 40 years or so of being considered a laboratory curiosity, HFIP began to receive chemists鈥� attention. A 2017 perspective by Ignacio Colomer, Timothy J. Donohoe, and co-workers at the University of Oxford (UK) described HFIP as a . Then, in 2022, Hashim F. Motiwala, Jeffrey Aub茅, and colleagues at the University of North Carolina (Chapel Hill and Wilmington) reviewed the . They described HFIP as a polar, strongly hydrogen bond鈥揹onating solvent with the 鈥渁bility to stabilize ionic species, transfer protons, and engage in a range of other intermolecular interactions鈥�.
After describing the physical properties of HFIP and comparing it with common solvents, Motiwala, Aub茅 et al. discussed the advantages of using it in 20 types of organic reactions, including solvolysis, carbon鈥揷arbon bond formation, carbon鈥揾ydrogen functionalization, condensation, and cyclization. The article includes an extraordinary 629 reaction schemes in which HFIP is used as the solvent, or in some cases as a reactant.
Not to be outdone, Colomer, Donohue et al. followed up their original article by describing HFIP as 鈥溾�. In addition to covering the same ground as Motiwala, Aub茅 et al., they delved into its use in electrochemical methods, organometallic and inorganic chemistry, biology, and materials and polymer science. Both author sets predict that HFIP will continue to garner many more applications in multiple scientific fields.
1. CAS Reg. No. 684-16-2.
Hexafluoro-2-propanol hazard information*
| Hazard class** | GHS code and hazard statement | |
|---|---|---|
| Acute toxicity, oral, category 4 | H302鈥擧armful if swallowed |  |
| Skin corrosion/irritation, category 1A | H314鈥擟auses severe skin burns and eye damage |  |
| Serious eye damage/eye irritation, category 1 | H318鈥擟auses serious eye damage | |
| Acute toxicity, inhalation, category 4 | H332鈥擧armful if inhaled | |
| Specific target organ toxicity, single exposure, respiratory tract irritation, category 3 | H335鈥擬ay cause respiratory irritation | |
| Reproductive toxicity, category 2 | H361鈥擲uspected of damaging fertility or the unborn child |  |
| Specific target organ toxicity, repeated exposure, category 2 | H373鈥擟auses damage to organs through prolonged or repeated exposure | |
*Compilation of multiple safety data sheets.
**Globally Harmonized System (GHS) of Classification and Labeling of Chemicals.聽.
Molecules from the journals
Aikinite1, a mineral with the empirical formula PbCuBiS3, was discovered in the Ural Mountains of Russia in 1843. It has since been found in Sweden, Australia (Tasmania), the United States (Idaho), and other countries. It is named after British geologist Arthur Aikin, even though he did not discover it.
This past April, Paz Vaqueiro at the University of Reading (UK), Marco Fornari at Central Michigan University (Mount Pleasant), and colleagues reported their study of the basis of aikinite鈥檚 extremely low thermal conductivity of 0.48 W/(m鈭�K) at 300 掳C. According to the authors, data obtained from inelastic neutron scattering, neutron diffraction, and molecular dynamics simulations showed that the 鈥渋s an effective mechanism to achieve ultralow thermal conductivity in crystalline materials.鈥�
trans-Nerolidol2 is a sesquiterpene alcohol found in essential oils from many flowering plants, including shrubs in the myrtle family (Myrtaceae), and legumes in the Fabaceae (aka Leguminosae) family. Its cis isomer is also found in nature. Each of the positional isomers exists as (+)- and (鈥�)-stereoisomers. trans-Nerolidol has been known since at least 1923, when 1939 chemistry Nobelist Leopold Ru啪i膷ka at ETH Zurich in three steps from geranyl chloride3.
The nerolidols are widely used as aroma and flavoring agents in foods, cosmetics, and personal-care products; but their supply is limited because the main sources are from plant extraction, which is costly and gives products of inconsistent purity. This May, Congqiang Zhang and co-workers at the Singapore Institute of Food and Biotechnology Innovation reported a biobased synthesis of trans-nerolidol in which the enzyme strawberry nerolidol synthase was engineered to from sugars and glycerol in yields as high as 26%.
1. CAS Reg. No. 12232-84-7.
2. CAS Reg. No. 40716-66-3 (racemic).
3. CAS Reg. No. 5389-87-7.
Molecules from the Journals
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Hexafluoro-2-propanol
fast facts
| CAS Reg. No. | 920-66-1 |
| SciFinder nomenclature | 2-Propanol, 1,1,1,3,3,3-hexafluoro- |
| Empirical formula | C3H2F6O |
| Molar mass | 168.04 g/mol |
| Appearance | Colorless liquid |
| Boiling point | 59 掳C |
| Water solubility | Miscible |
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