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Information about Trifluoroethanol







2,2,2-Trifluoroethanol
Identifiers
CAS number75-89-8
SMILESOCC(F)(F)F
Properties
Molecular formulaC2H3F3O
Molar mass100.04 g/mol
AppearanceColorless liquid
Density1.393 g/ml, liquid
Melting point −45.0 °C
Boiling point 78.0 °C
Solubility in waterMiscible
Solubility in ethanolMiscible
Thermochemistry
Std enthalpy of
formation ΔfHo298		? kJ/mol
Std enthalpy of
combustion ΔcHo298		? kJ/mol
Standard molar
entropy So298		? J.K−1.mol−1
Hazards
EU classificationHarmful (Xn)
NFPA 704
3
2
1
 
R-phrasesR10, R20/21/22, R36/38, R62
S-phrasesS16, S36/37/39, S45
Related Compounds
Related alcoholsHexafluoro-2-propanol
Related compounds1,1,1-Trifluoroethane
Trifluoroacetic acid
Except where noted otherwise, data are given for
materials in their standard state
(at 25 C, 100 kPa)


2,2,2-Trifluoroethanol (TFE) or trifluoroethyl alcohol is a trifluoro substituted alcohol. It is a coloreless, water miscible liquid with a smell reminiscent of ethanol. Due to the electronegativity of fluorine atoms, this compound exhibits a stronger acidic character compared to ethanol. Thus TFE can form stable complexes also with heterocycles (e.g. THF or pyridine) through hydrogen bonding.

TFE can be synthesized by means of hydrogenolysis on 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 tertiary aliphatic amines like triethylamine are commonly employed.

Trifluoroethanol is used as a solvent in organic chemistry [1], [2]. It is also a source of trifluoromethyl group for various chemical reactions (Still-Gennari modification of HWE reaction). Oxidation of trifluoroethanol yields trifluoroacetaldehyde or trifluoroacetic acid. In biology TFE is used as a co-solvent in protein folding studies with NMR: this solvent can effectively solubilize both peptides and proteins and it is known that, 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.

References

1. ^ Review: Begue, J.-P.; Bonnet-Delpon, D.; Crousse, B. Fluorinated Alcohols: A New Medium for Selective and Clean Reaction. Synthesis, 2004,(1), pp. 18-29.
2. ^ Review: Shuklov, Ivan A. ; Dubrovina, Natalia V.; Börner, Armin Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis, Synthesis, 2007, pp. 2925-2943
  • 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"
CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. They are also referred to as CAS numbers, CAS RNs or CAS #s.
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smiles

File extension: .smi
Type of format: chemical file format

The simplified molecular input line entry specification or SMILES
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A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. A chemical formula is also a short way of showing how a chemical reaction occurs.
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Molar mass, symbol M,[1] is the mass of one mole of a substance (chemical element or chemical compound).[2] It is a physical property which is characteristic of each pure substance.
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In physics, density is mass m per unit volume V—how heavy something is compared to its size. A small, heavy object, such as a rock or a lump of lead, is denser than a lighter object of the same size or a larger object of the same weight, such as pieces of
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The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. Although the phrase would suggest a specific temperature and is commonly and incorrectly used as such in most textbooks and literature, most crystalline compounds
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boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid.[1][2][3][4]
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Solubility is a physical property referring to the ability for a given substance, the solute, to dissolve in a solvent.[1] It is measured in terms of the maximum amount of solute dissolved in a solvent at equilibrium. The resulting solution is called a saturated solution.
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Water is a common chemical substance that is essential to all known forms of life.[1] In typical usage, water refers only to its liquid form or state, but the substance also has a solid state, ice, and a gaseous state, water vapor.
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Solubility is a physical property referring to the ability for a given substance, the solute, to dissolve in a solvent.[1] It is measured in terms of the maximum amount of solute dissolved in a solvent at equilibrium. The resulting solution is called a saturated solution.
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Ethanol, also known as ethyl alcohol, drinking alcohol or grain alcohol, is a flammable, colorless, slightly toxic chemical compound, and is best known as the alcohol found in alcoholic beverages.
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The standard enthalpy of formation or "standard heat of formation" of a compound is the change of enthalpy that accompanies the formation of 1 mole of a substance in its standard state from its constituent elements in their standard states (the most stable form of the element at
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Standard enthalpy of Combustion is the change in enthalpy of the total reacting system (i.e. both products and reactants are considered the thermodynamic system) when one mole of a substance completely reacts with oxygen, and is observed at 298K and 1 atmospheric pressure (note:
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In chemistry, the standard molar entropy is the entropy content of one mole of substance, under conditions of standard temperature and pressure (STP).

The standard molar entropy is usually given the symbol So, and the units J mol−1 K
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Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main European Union law concerning chemical safety.
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NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. It defines the colloquial "fire diamond" used by emergency personnel to quickly and easily identify the risks posed by nearby hazardous materials.
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R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations.
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S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. The list was consolidated and republished in Directive 2001/59/EC , where translations into other EU languages may be found.
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alcohol is any organic compound in which a hydroxyl group (-OH) is bound to a carbon atom of an alkyl or substituted alkyl group. The general formula for a simple acyclic alcohol is CnH2n+1OH.
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1,1,1,3,3,3-Hexafluoro-2-propanol or Hexafluoroisopropanol (HFIP) is a fluorinated alcohol frequently used as solvent for polymer systems. It appears as a colorless, volatile liquid that is characterized by a strong, pungent odor.
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1,1,1-Trifluoroethane, or R-143a or simply trifluoroethane, is a fluorocarbon compound that is a clear, colorless gas. It should not be confused with the isomeric compound 1,1,2-trifluoroethane.

It has a critical temperature of 73 °C.
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Trifluoroacetic acid (TFA) is the chemical compound with the formula CF3CO2H. It is a strong carboxylic acid due to the influence of the three very electronegative fluorine atoms. Relative to acetic acid, TFA is almost 100,000-fold more acidic.
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standard state of a material is its state at 1 bar (100 kilopascals exactly). This pressure was changed from 1 atm (101.325 kilopascals) by IUPAC in 1990.[1] The standard state of a material can be defined at any given temperature, most commonly 25 degrees Celsius,
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alcohol is any organic compound in which a hydroxyl group (-OH) is bound to a carbon atom of an alkyl or substituted alkyl group. The general formula for a simple acyclic alcohol is CnH2n+1OH.
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Ethanol, also known as ethyl alcohol, drinking alcohol or grain alcohol, is a flammable, colorless, slightly toxic chemical compound, and is best known as the alcohol found in alcoholic beverages.
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Electronegativity, symbol χ, is a chemical property which describes the power of an atom (or, more rarely, a functional group) to attract electrons towards itself.[1] First proposed by Linus Pauling in 1932 as a development of valence bond theory,[2]
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100% F is stable with 10 neutrons
References
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Heterocyclic compounds are organic compounds that contain a ring structure containing atoms in addition to carbon, such as sulfur, oxygen or nitrogen, as part of the ring. They may be either simple aromatic rings or non-aromatic rings.
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Pyridine is a chemical compound with the formula C5H5N. It is a liquid with a distinctively putrid, fishy odour. Pyridine is a simple and fundamentally important heterocyclic aromatic organic compound that is structurally related to benzene, wherein one CH
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hydrogen bond is a special type of dipole-dipole bond that exists between an electronegative atom and a hydrogen atom bonded to another electronegative atom. This type of bond always involves a hydrogen atom, thus the name.
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