2,2,2-Trifluoroethanol
Encyclopedia
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. Thus, TFE forms stable complexes also with heterocycles
(e.g. THF
or pyridine
) through hydrogen bond
ing.
or the hydride reduction of derivatives of trifluoroacetic acid
, such as the esters or acid 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
. As a co-catalyst for this conversion tertiary aliphatic amines like triethylamine
are commonly employed.
in organic chemistry. Oxidations of sulfur compounds using hydrogen peroxide
are effectively conducted in TFE.
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 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.
. It also serves as a source of the trifluoromethyl group for various chemical reactions (Still-Gennari modification of HWE reaction).
2,2,2-trifluoro-1-vinyloxyethane, an inhaled drug introduced clinically under the tradename Fluromar, features a vinylether of trifluorethanol. This species was prepared by the reaction of trifluoroethanol with acetylene
.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
with the formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....
CF3CH2OH. Also known as TFE or trifluoroethyl alcohol, this colourless, water-miscible liquid has a smell reminiscent of ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...
. Due to the electronegativity
Electronegativity
Electronegativity, symbol χ , is a chemical property that describes the tendency of an atom or a functional group to attract electrons towards itself. An atom's electronegativity is affected by both its atomic number and the distance that its valence electrons reside from the charged nucleus...
of the trifluoromethyl
Trifluoromethyl
Trifluoromethyl is a functional group in organofluorines that has the formula -CF3. The naming of is group is derived from the methyl group , by replacing each hydrogen atom by a fluorine atom. The trifluomethyl group has a significant electronegativity that is often described as being...
group, this alcohol
Alcohol
In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....
exhibits a stronger acidic character compared to ethanol. Thus, TFE forms stable complexes also with heterocycles
Heterocyclic compound
A heterocyclic compound is a cyclic compound which has atoms of at least two different elements as members of its ring. The counterparts of heterocyclic compounds are homocyclic compounds, the rings of which are made of a single element....
(e.g. THF
ThF
Follicular B helper T cells , are antigen-experienced CD4+ T cells found in the B cell follicles of secondary lymphoid organs such as lymph nodes, spleens and Peyer's patches, and are identified by their constitutive expression of the B cell follicle homing receptor CXCR5...
or pyridine
Pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one C-H group replaced by a nitrogen atom...
) through hydrogen bond
Hydrogen bond
A hydrogen bond is the attractive interaction of a hydrogen atom with an electronegative atom, such as nitrogen, oxygen or fluorine, that comes from another molecule or chemical group. The hydrogen must be covalently bonded to another electronegative atom to create the bond...
ing.
Synthesis
Trifluoroethanol is produced industrially by hydrogenationHydrogenation
Hydrogenation, to treat with hydrogen, also a form of chemical reduction, is a chemical reaction between molecular hydrogen and another compound or element, usually in the presence of a catalyst. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically...
or the hydride reduction of derivatives of trifluoroacetic acid
Trifluoroacetic acid
Trifluoroacetic acid is the simplest stable perfluorinated carboxylic acid chemical compound, with the formula CF3CO2H. It is a strong carboxylic acid due to the influence of the electronegative trifluoromethyl group. TFA is almost 100,000-fold more acidic than acetic acid...
, such as the esters or acid chloride.
TFE can also be prepared by hydrogenolysis
Hydrogenolysis
Hydrogenolysis is a chemical reaction whereby a carbon–carbon or carbon–heteroatom single bond is cleaved or undergoes "lysis" by hydrogen. The heteroatom may vary, but it usually is oxygen, nitrogen, or sulfur. A related reaction is hydrogenation, where hydrogen is added to the molecule, without...
of compounds of generic formula CF3−CHOH−OR (where R is hydrogen
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...
or an alkyl group containing from one to eight carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
atoms), in the presence of a palladium
Palladium
Palladium is a chemical element with the chemical symbol Pd and an atomic number of 46. It is a rare and lustrous silvery-white metal discovered in 1803 by William Hyde Wollaston. He named it after the asteroid Pallas, which was itself named after the epithet of the Greek goddess Athena, acquired...
containing catalyst deposited on activated charcoal
Charcoal
Charcoal is the dark grey residue consisting of carbon, and any remaining ash, obtained by removing water and other volatile constituents from animal and vegetation substances. Charcoal is usually produced by slow pyrolysis, the heating of wood or other substances in the absence of oxygen...
. As a co-catalyst for this conversion tertiary aliphatic amines like triethylamine
Triethylamine
Triethylamine is the chemical compound with the formula N3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine, for which TEA is also a common abbreviation....
are commonly employed.
Uses
Trifluoroethanol is used as a solventSolvent
A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...
in organic chemistry. Oxidations of sulfur compounds using hydrogen peroxide
Hydrogen peroxide
Hydrogen peroxide is the simplest peroxide and an oxidizer. Hydrogen peroxide is a clear liquid, slightly more viscous than water. In dilute solution, it appears colorless. With its oxidizing properties, hydrogen peroxide is often used as a bleach or cleaning agent...
are effectively conducted in TFE.
Protein denaturant.
In biology TFE is used as a co-solvent in protein
Protein
Proteins are biochemical compounds consisting of one or more polypeptides typically folded into a globular or fibrous form, facilitating a biological function. A polypeptide is a single linear polymer chain of amino acids bonded together by peptide bonds between the carboxyl and amino groups of...
folding
Folding
Fold or folding may refer to:* Paper folding, the art of folding paper* Book folding, in book production* Skin fold, an area of skin that folds* Fold , in the game of poker, to discard one's hand and forfeit interest in the current pot...
studies with NMR
NMR
NMR may refer to:Applications of Nuclear Magnetic Resonance:* Nuclear magnetic resonance* NMR spectroscopy* Solid-state nuclear magnetic resonance* Protein nuclear magnetic resonance spectroscopy* Proton NMR* Carbon-13 NMR...
spectroscopy: this solvent can effectively solubilize both peptides and proteins. Depending upon its concentration, TFE can strongly affect the three-dimensional
Dimension
In physics and mathematics, the dimension of a space or object is informally defined as the minimum number of coordinates needed to specify any point within it. Thus a line has a dimension of one because only one coordinate is needed to specify a point on it...
structure of proteins.
Industrially trifluoroethanol is employed as a solvent for nylon
Nylon
Nylon is a generic designation for a family of synthetic polymers known generically as polyamides, first produced on February 28, 1935, by Wallace Carothers at DuPont's research facility at the DuPont Experimental Station...
as well as in applications of the pharmaceutical field.
Reactions
Oxidation of trifluoroethanol yields trifluoroacetaldehyde or trifluoroacetic acidTrifluoroacetic acid
Trifluoroacetic acid is the simplest stable perfluorinated carboxylic acid chemical compound, with the formula CF3CO2H. It is a strong carboxylic acid due to the influence of the electronegative trifluoromethyl group. TFA is almost 100,000-fold more acidic than acetic acid...
. It also serves as a source of the trifluoromethyl group for various chemical reactions (Still-Gennari modification of HWE reaction).
2,2,2-trifluoro-1-vinyloxyethane, an inhaled drug introduced clinically under the tradename Fluromar, features a vinylether of trifluorethanol. This species was prepared by the reaction of trifluoroethanol with acetylene
Acetylene
Acetylene is the chemical compound with the formula C2H2. 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 pure form and thus is usually handled as a solution.As an alkyne, acetylene is unsaturated because...
.