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2358-54-5 | 2-(2,2,2-TRIFLUOROETHOXY)ETHANOL

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Purchase CAS:2358-54-5 | 2-(2,2,2-TRIFLUOROETHOXY)ETHANOL,view related peer-reviewed papers,technical documents,similar products,MSDS & more.Synthesis AnalysisThe synthesis of compounds related to 2-(2,2,2-Trifluoroethoxy)ethanol involves the use of Lewis acid catalysts such as scandium trifluoromethanesulfonate for acylation reactions, which is highly effective for primary alcohols and even sterically-hindered secondary or tertiary alco...
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CAS:2358-54-5 | 2-(2,2,2-TRIFLUOROETHOXY)ETHANOL,Description

 

Synthesis Analysis

The synthesis of compounds related to 2-(2,2,2-Trifluoroethoxy)ethanol involves the use of Lewis acid catalysts such as scandium trifluoromethanesulfonate for acylation reactions, which is highly effective for primary alcohols and even sterically-hindered secondary or tertiary alcohols. Additionally, the ethanolysis of perfluoro-(2-methyl-2H-azirine) results in the formation of ethyl 2-ethoxy-3,3,3-trifluoro-2-hydroxy- and 3,3,3-trifluoro-2,2-dihydroxy-propionate, indicating the reactivity of ethanol with perfluorinated azirines.

Molecular Structure Analysis

The molecular conformation and intermolecular hydrogen bonding of 2-(2,2,2-Trifluoroethoxy)ethanol have been studied using neutron diffraction, molecular dynamics, and ab initio quantum chemical methods. The structure of related trifluoromethylated alcohols has been confirmed by single crystal X-ray analyses, revealing the presence of intermolecular hydrogen bonding10 .

Chemical Reactions Analysis

The compound's reactivity has been explored in various contexts. For instance, the coordination chemistry of mercury-containing anticrowns with ethanol demonstrates the ability of ethanol to form complexes with mercury compounds. Moreover, the use of bis(2-methoxyethyl)aminosulfur trifluoride as a deoxofluorinating agent indicates the potential for transforming alcohols into alkyl fluorides.

Physical and Chemical Properties Analysis

The physical and chemical properties of 2-(2,2,2-Trifluoroethoxy)ethanol and its mixtures have been extensively studied. The peculiar behavior of its aqueous solutions, such as a structural transition at a specific mole fraction, has been observed and is significantly different from nonsubstituted ethanol. The role of the hydrophobic terminal in the hydrogen bond network of aqueous mixtures of the compound has been investigated, showing that the -CF3 substitution changes the orientation and hydrogen-bonding site of water molecules. Additionally, the liquid-liquid equilibrium for mixtures involving the compound has been characterized, providing insights into the intermolecular interactions and phase behavior.

Relevant Case Studies

Case studies in the provided papers include the investigation of liquid mixtures involving hydrogenated and fluorinated chains, which display complex behavior due to the balance between weak dispersion forces and preferential hydrogen bonding. Another case study involves the peculiarities of aqueous solutions of the compound, which show transition-like behavior at low solute contents. These studies are relevant as they provide a deeper understanding of the compound's behavior in different environments and its interactions with other molecules.

Scientific Research Applications

 

1. Use as a Specialized Solvent in Organic Chemistry

  • Summary of Application : 2-(2,2,2-Trifluoroethoxy)ethanol, also known as Trifluoroethanol, is used as a specialized solvent in organic chemistry.

2. Synthesis and Evaluation of Antiplasmodial Activity

  • Summary of Application : 2-(2,2,2-Trifluoroethoxy)ethanol has been used in the synthesis of chalcones to evaluate their antiplasmodial activity against Plasmodium falciparum.
  • Methods of Application : A new class of compounds comprising two series of chalcones with 2,2,2-trifluoroethoxy group were synthesized and screened for in vitro antiplasmodial activity against Plasmodium falciparum (3D7) using the [3H] hypoxanthine incorporation inhibition assay.
  • Results or Outcomes : Chalcones with 2,2,2-trifluoroethoxy groups substituted on the o-position of the 1-phenyl ring displayed enhanced antiplasmodial activity. Of the 34 compounds synthesized, chalcones 3a and 3f exhibited significant inhibitory effects, with IC50 values of 3.0 μg/mL and 2.2 μg/mL, respectively.

3. Oxidation of Sulfur Compounds

  • Summary of Application : 2-(2,2,2-Trifluoroethoxy)ethanol, also known as Trifluoroethanol, is used in the oxidation of sulfur compounds.
  • Methods of Application : Oxidations of sulfur compounds using hydrogen peroxide are effectively conducted in 2-(2,2,2-Trifluoroethoxy)ethanol.
  • Results or Outcomes : The use of Trifluoroethanol as a solvent can enhance the efficiency of the oxidation process of sulfur compounds.

4. Protein Denaturation

  • Summary of Application : 2-(2,2,2-Trifluoroethoxy)ethanol can be used as a protein denaturant.
  • Methods of Application : In biochemistry, it is often necessary to denature proteins, or cause them to lose their native structure. This is typically done by adding a denaturing agent, such as 2-(2,2,2-Trifluoroethoxy)ethanol.
  • Results or Outcomes : The use of Trifluoroethanol as a denaturing agent can help researchers study the properties of proteins in their denatured state.

5. NMR Solvent

  • Summary of Application : 2-(2,2,2-Trifluoroethoxy)ethanol can be used as a solvent in Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Methods of Application : In NMR spectroscopy, it is often necessary to dissolve the sample in a suitable solvent. 2-(2,2,2-Trifluoroethoxy)ethanol, due to its unique properties, can be used as such a solvent.
  • Results or Outcomes : The use of 2-(2,2,2-Trifluoroethoxy)ethanol as an NMR solvent can help researchers obtain clear and accurate NMR spectra.

6. HPLC and LC-MS Solvent

  • Summary of Application : 2-(2,2,2-Trifluoroethoxy)ethanol can be used as a solvent in High Performance Liquid Chromatography (HPLC) and Liquid Chromatography-Mass Spectrometry (LC-MS).
  • Methods of Application : In HPLC and LC-MS, the sample is often dissolved in a suitable solvent. 2-(2,2,2-Trifluoroethoxy)ethanol, due to its unique properties, can be used as such a solvent.
  • Results or Outcomes : The use of 2-(2,2,2-Trifluoroethoxy)ethanol as an HPLC and LC-MS solvent can help researchers obtain accurate chromatograms and mass spectra.

Safety And Hazards

This compound is considered hazardous according to the 2012 OSHA Hazard Communication Standard. It has been associated with risks such as acute oral toxicity, acute inhalation toxicity, serious eye damage/eye irritation, reproductive toxicity, and specific target organ toxicity.

More Information

Product Name:2-(2,2,2-TRIFLUOROETHOXY)ETHANOL
Synonyms:2-(2,2,2-TRIFLUOROETHOXY)ETHANOL;2-(2,2,2-Trifluoroethoxy)ethanol97+%;Ethanol, 2-(2,2,2-trifluoroethoxy)-;2-(2,2,2-Trifluoroethoxy)ethan-1-ol 97+%;5,5,5-Trifluoro-3-oxapentan-1-ol, 5-Hydroxy-1,1,1-trifluoro-3-oxapentane;2-(2,2,2-Trifluoroethoxy)ethan-1-ol
CAS:2358-54-5
MF:C4H7F3O2
MW:144.09
EINECS: 
Product Categories:Aliphatics
Mol File:2358-54-5.mol
 
2-(2,2,2-TRIFLUOROETHOXY)ETHANOL Chemical Properties
Boiling point 84/80mm
density 1.2902 g/cm3(Temp: 25 °C)
storage temp. Hygroscopic, Room Temperature, under inert atmosphere
solubility Chloroform (Sparingly), Methanol (Slightly)
form Oil
pka14.21±0.10(Predicted)
color Pale Yellow

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