2,2,2-Trifluoroethanol is the organic compound 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 ...

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 Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

exhibits a stronger acidic character compared to ethanol.

Synthesis

Trifluoroethanol is produced industrially by hydrogenation or the hydride reduction of derivatives of trifluoroacetic acid, such as the esters or acyl chloride. TFE can also be prepared by hydrogenolysis of compounds of generic formula CF₃−CHOH−OR (where R is hydrogen or an alkyl group containing from one to eight carbon atoms), in the presence of a palladium containing catalyst deposited on activated

charcoal Charcoal is a lightweight black carbon residue produced by strongly heating wood (or other animal and plant materials) in minimal oxygen to remove all water and volatile constituents. In the traditional version of this pyrolysis process, cal ...

. As a co-catalyst for this conversion tertiary aliphatic amines like triethylamine are commonly employed.

Uses

Trifluoroethanol is used as a solvent in organic chemistry. Oxidations of sulfur compounds using hydrogen peroxide are effectively conducted in TFE. It can also be used as a protein denaturant. In biology TFE is used as a co-solvent in protein folding studies with NMR spectroscopy: this solvent can effectively solubilize both

peptides 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 p ...

and proteins. Depending upon its concentration, TFE can strongly affect the three-dimensional structure of proteins. Industrially trifluoroethanol is employed as a solvent for nylon as well as in applications of the pharmaceutical field. Trifluoroethanol is a key precursor for the

inhaled anaesthetic 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 anaesthetic vapori ...

isoflurane Isoflurane, sold under the brand name Forane among others, is a general anesthetic. It can be used to start or maintain anesthesia; however, other medications are often used to start anesthesia rather than isoflurane, due to airway irritation w ...

, listed on the World Health Organization's List of Essential Medicines. Trifluoroethanol is also used in biochemistry as an inhibitor to study enzymes. It competitively inhibits alcohol dehydrogenase for example.

Reactions

Oxidation of trifluoroethanol yields trifluoroacetaldehyde or trifluoroacetic acid. It also serves as a source of the trifluoroethoxy group for various chemical reactions (Still-Gennari modification of

HWE reaction Hwe or HWE may refer to: * Hwe (Cyrillic), a letter of the Cyrillic script * Hwe language, spoken in Ghana, Togo, and Benin * Hardy–Weinberg equilibrium * Home War Establishment of the Royal Canadian Air Force * Horner–Wadsworth–Emmons rea ...

). 2,2,2-Trifluoroethyl vinyl ether, an inhaled drug introduced clinically under the tradename Fluoromar, features a vinyl ether of trifluorethanol. This species was prepared by the reaction of trifluoroethanol with

acetylene Acetylene (systematic name: ethyne) is the chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pure ...

. TFE forms stable complexes with Lewis bases such as THF or pyridine through

hydrogen bond In chemistry, a hydrogen bond (or H-bond) is a primarily electrostatic force of attraction between a hydrogen (H) atom which is covalently bound to a more electronegative "donor" atom or group (Dn), and another electronegative atom bearing a ...

ing, yielding 1:1 adducts. CF₃CH₂OH is classified as a hard Lewis acid and its acceptor properties are discussed in the ECW model yielding E_A = 2.07 and C_A = 1.06.

Safety

Trifluoroethanol is classified as toxic to blood, the reproductive system, bladder, brain, upper respiratory tract and eyes. Research has shown it to be a testicular toxicant in rats and dogs.Fischer Scientific MSDS
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References

External links

Halocarbon Fluorochemicals
* United States Patent number 4,647,706 "Process for the synthesis of 2,2,2-Trifluoroethanol and 1,1,1,3,3,3-Hexafluoroisopropanol" {{DEFAULTSORT:Trifluoroethanol, 2, 2, 2- Halogenated solvents Primary alcohols GABAA receptor positive allosteric modulators Glycine receptor agonists Sedatives Hypnotics Halohydrins Trifluoromethyl compounds