Hexafluoroisopropanol, commonly abbreviated HFIP, is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwee ...

(CF₃)₂CHOH. This

fluoroalcohol Fluoroalcohols are organofluorine compounds consisting of an alcohol functional group with at least one C-F bond. These compounds often have distinctive solvent properties. Perfluoroalcohols Most primary and secondary perfluoroalcohols are unst ...

finds use as

solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") 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 ...

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. Dual XH–π interaction of HFIP with arenes has been found (

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...

/HFIP, 7.22 kcal/mol) even stronger than the hydrogen bond in a

water dimer The water dimer consists of two water (molecule), water molecules loosely bound by a hydrogen bond. It is the smallest water cluster. Because it is the simplest model system for studying hydrogen bonding in water, it has been the target of many ...

(5-6 kcal/mol). Hexafluoro-2-propanol is transparent to UV light with high

density Density (volumetric mass density or specific mass) is the substance's mass per unit of volume. The symbol most often used for density is ''ρ'' (the lower case Greek letter rho), although the Latin letter ''D'' can also be used. Mathematical ...

, low

viscosity The viscosity of a fluid is a measure of its resistance to deformation at a given rate. For liquids, it corresponds to the informal concept of "thickness": for example, syrup has a higher viscosity than water. Viscosity quantifies the inte ...

and low

refractive index In optics, the refractive index (or refraction index) of an optical medium is a dimensionless number that gives the indication of the light bending ability of that medium. The refractive index determines how much the path of light is bent, or ...

Production and uses

Hexafluoro-propan-2-ol is prepared from

hexafluoropropylene Hexafluoropropylene is the fluoroalkene with the formula CF3CF=CF2. It is the perfluorocarbon counterpart to the hydrocarbon propylene. It is mainly used to produce copolymers with tetrafluoroethylene. Hexafluoropropylene is used as a chemical ...

through

hexafluoroacetone 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 mus ...

, which is then

hydrogenated Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic co ...

.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. :(CF₃)₂CO + H₂ → (CF₃)₂CHOH Hexafluoro-propan-2-ol is a speciality solvent for some polar polymers and

organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

. 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:

polyamide A polyamide is a polymer with repeating units linked by amide bonds. Polyamides occur both naturally and artificially. Examples of naturally occurring polyamides are proteins, such as wool and silk. Artificially made polyamides can be made through ...

polyacrylonitrile Polyacrylonitrile (PAN), also known as polyvinyl cyanide and Creslan 61, is a synthetic, semicrystalline organic polymer resin, with the linear formula (C3H3N)n. Though it is thermoplastic, it does not melt under normal conditions. It degrades bef ...

s, polyacetals,

polyester Polyester is a category of polymers that contain the ester functional group in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include natural ...

s (e.g.

polyglycolide Polyglycolide or poly(glycolic acid) (PGA), also spelled as polyglycolic acid, is a biodegradable, thermoplastic polymer and the simplest linear, aliphatic polyester. It can be prepared starting from glycolic acid by means of polycondensation or ...

), and polyketones. It has also found use in

biochemistry Biochemistry or biological chemistry is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology and ...

to solubilize

peptide Peptides (, ) are short chains of amino acids linked by peptide bonds. Long chains of amino acids are called proteins. Chains of fewer than twenty amino acids are called oligopeptides, and include dipeptides, tripeptides, and tetrapeptides. A ...

s and to monomerize

β-sheet The beta sheet, (β-sheet) (also β-pleated sheet) is a common motif of the regular protein secondary structure. Beta sheets consist of beta strands (β-strands) connected laterally by at least two or three backbone hydrogen bonds, forming a gen ...

protein aggregates. Because of its acidity (pK_a = 9.3), it can be used as acid in volatile buffers for ion pair

HPLC High-performance liquid chromatography (HPLC), formerly referred to as high-pressure liquid chromatography, is a technique in analytical chemistry used to separate, identify, and quantify each component in a mixture. It relies on pumps to pa ...

mass spectrometry Mass spectrometry (MS) is an analytical technique that is used to measure the mass-to-charge ratio of ions. The results are presented as a ''mass spectrum'', a plot of intensity as a function of the mass-to-charge ratio. Mass spectrometry is use ...

nucleic acid Nucleic acids are biopolymers, macromolecules, essential to all known forms of life. They are composed of nucleotides, which are the monomers made of three components: a 5-carbon sugar, a phosphate group and a nitrogenous base. The two main cl ...

s. Recent studies showed an ability of HFIP to activate allylic alcohols, stabilise an allylic cation, and further functionalize to allylic sulphides and sulfones.

Medicine

It is both the precursor and the chief metabolite of the

inhalation anesthetic An inhalational anesthetic is a chemical compound possessing general anesthetic properties that can be delivered via inhalation. They are administered through a face mask, laryngeal mask airway or tracheal tube connected to an anesthetic vapori ...

sevoflurane Sevoflurane, sold under the brand name Sevorane, among others, is a sweet-smelling, nonflammable, highly fluorinated methyl isopropyl ether used as an inhalational anaesthetic for induction and maintenance of general anesthesia. After desflura ...

. 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.

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, placing HFIP as a reproductive toxicity category 2 material.

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. 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.

References

Sources

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External links

Application note on quantification of HFIP in polymers
{{Authority control Trifluoromethyl compounds Halogenated solvents Secondary alcohols