2,2,2-Trifluoroethanol

2,2,2-Trifluoroethanol

Names
Preferred IUPAC name 2,2,2-Trifluoroethan-1-ol
Other names 2,2,2-Trifluoroethanol
Identifiers
CAS Number	75-89-8 Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:42330 N
ChemSpider	21106169 N
DrugBank	DB03226 N
ECHA InfoCard	100.000.831
PubChem CID	6409
InChI InChI=1S/C2H3F3O/c3-2(4,5)1-6/h6H,1H2 N Key: RHQDFWAXVIIEBN-UHFFFAOYSA-N N InChI=1/C2H3F3O/c3-2(4,5)1-6/h6H,1H2 Key: RHQDFWAXVIIEBN-UHFFFAOYAH
SMILES OCC(F)(F)F FC(F)(F)CO
Properties
Chemical formula	C2H3F3O
Molar mass	100.04 g/mol
Appearance	Colorless liquid
Density	1.325±0.06 g/mL @ 20 °C, 760 Torr liquid
Melting point	−43.5 °C (−46.3 °F; 229.7 K)
Boiling point	74.0 °C (165.2 °F; 347.1 K)
Solubility in water	Miscible
Solubility in ethanol	Miscible
Acidity (pKa)	12.46±0.10 Most Acidic Temp: 25 °C
Viscosity	0.9 cSt @ 37.78 °C
Thermochemistry
Std molar entropy (So298)	? J.K−1.mol−1
Std enthalpy of formation (ΔfHo298)	? kJ/mol
Std enthalpy of combustion (ΔcHo298)	-886.6 kJ/mol
Hazards
EU classification (DSD) (outdated)	Harmful (Xn)
R-phrases (outdated)	R10, R20/21/22, R36/38, R62
S-phrases (outdated)	S16, S36/37/39, S45
NFPA 704	3 2 1
Related compounds
Related alcohols	Hexafluoro-2-propanol
Related compounds	1,1,1-Trifluoroethane Trifluoroacetic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

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 bonding.

Trifluoroethanol is produced industrially by hydrogenation 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.

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 and proteins. Depending upon its concentration, TFE can strongly affect the three-dimensional structure of proteins.