2,2,2-Trifluoroethanol

Base Information

• Chemical Name: 2,2,2-Trifluoroethanol
• CAS No.: 75-89-8
• Molecular Formula: C2H3F3O
• Molecular Weight: 100.04
• Hs Code.: 29055910
• European Community (EC) Number: 200-913-6
• NSC Number: 451
• UNII: 8T8I76KYF1
• DSSTox Substance ID: DTXSID0021751
• Nikkaji Number: J2.396E
• Wikipedia: 2,2,2-Trifluoroethanol
• Wikidata: Q2474643
• Metabolomics Workbench ID: 52312
• ChEMBL ID: CHEMBL116675
• Mol file: 75-89-8.mol

Synonyms:2,2,2-Trifluoroethanol;Alcohol, Trifluoroethyl;Trifluoroethanol;Trifluoroethyl Alcohol

Chemical Property of 2,2,2-Trifluoroethanol

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 70 mm Hg ( 25 °C)
• Melting Point: -44 °C(lit.)
• Refractive Index: n20/D 1.3(lit.)
• Boiling Point: 74 °C at 760 mmHg
• PKA: 12.4(at 25℃)
• Flash Point: 29.4 °C
• PSA: 20.23000
• Density: 1.325 g/cm³
• LogP: 0.54100
• Storage Temp.: Store at RT.
• Water Solubility.: Miscible with water, ethers, ketones, alcohols and chloroform.
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 100.01359920
• Heavy Atom Count: 6
• Complexity: 38.5

Purity/Quality:

99% ^*data from raw suppliers

2,2,2-Trifluoroethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,F,Xn
• Hazard Codes: Xn,T,F
• Statements: 10-20/21/22-37/38-41-62-38-36/37/38
• Safety Statements: 26-36-39-45-36/37/39-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Alcohols
• Canonical SMILES: C(C(F)(F)F)O
• Description: 2,2,2-trifluoroethanol or trifluoroethanol is called TFEA or TEF, it is important intermediate of the fluorine-containing aliphatic, it is colorless, it is miscible liquids with water, it has similar odor with ethanol. Due to the strong electron-withdrawing effect of trifluoromethyl, acid of trifluoromethyl is stronger than ethanol, it can generate hydrogen-bonded stable complex (such as: tetrahydrofuran, pyridine) with heterocyclic compound. Due to this unique physical and chemical properties and special molecular structure, it has different performance with other alcohols, it can participate in a variety of organic reactions, it can be oxidized to acetaldehyde trifluoromethyl or trifluoroacetic acid, it can also provide trifluoromethyl, it can participate in the Still-Gennari improvements of Horner-Wadsworth-Emmons reaction. It has wide range of uses in medicine, pesticides, dyes, energy, and other aspects of organic synthesis. The main use of trifluoroethanol is as anesthetic, at the earliest, fluorine acetylene ether which synthesized by trifluoroethanol and acetylene takes place of bigger side effects of bromine-fluoro alkanes as anesthetic, and then trichloroethanol is used as raw material to develop non-flammable, low toxicity isoflurane alkanes and high performance of the new anesthetic of chlorofluoroalkane. Trifluoroethanol can be introduced into drug structure as trifluoromethyl of functional group, it can generate significant physiological activity, increase fat-soluble of molecules, improve efficacy or reduce side effects of the organism, its synthetic drugs have central nervous system stimulants fluticasone Seoul, substituted pyridines stomach cytoplasmic proton pump inhibitor Lansoprazole and Pariprazole, antiarrhythmic drugs flecainide with amines and analgesic drugs benzodiazepines and dysuria treatment KMD-3212 and so on.
• Uses: (1) It can be used as import agent of trifluoroethyl and trifluoroacetic ethoxycarbonyl agent, synthetic narcotics fluoride ether (Fluroxene), isoflurane (Isoflurane) and to chlorine halothane (Desflurane), central nervous system stimulants fluticasone Seoul (Flowotyl), proton pump inhibitor lansoprazole (Lansoprazol, pp inhibitors), anti-arrhythmic drugs flecainide with amine (Flecamide), analgesics, benzodiazepines (Quazepam), difficulty urinating therapeutic drug KMD-3213, herbicide trifluoromethyl thiomethyl (Triflusulfuronmethyl). (2) It can be used for chemical reagents. (3) It can be used as solvent, it can be used as import agent of trifluoroethyl and trifluoroacetic ethoxycarbonyl agent, it can be also used as pharmaceutical, pesticide intermediates. (4) It can be used as solvent, it is also used as medicine, pesticide intermediates. In synthesis of medical anaesthetics, pharmaceuticals, and agrochemicals; in polymerizations. Protein denaturant; stabilizes peptide structures. Cleaning solvent; eluent in HPLC separations; working fluid in Rankine heat cycle systems. Environmentally friendly alternative to CFCs. Trifluoroethanol serves as a solvent and a raw material in organic chemistry and biology. TFE is a solvent of choice for hydrogen peroxide-mediated oxidations of sulfides. Trifluoroethanol acts as a protein denaturant. It is used in the manufacture of certain pharmaceuticals and drug substances. The drug fluromer, which is 2,2,2-trifluoro-1-vinyloxyethane, is the vinyl ether of trifluorethanol. It is an effective solvent for peptides and proteins, and used for NMR-based protein folding studies, and in the manufacture of nylon. As a source of the trifluoromethyl group, it is employed in several organic reactions, for example in Still-Gennari modification of Horner-Wadsworth-Emmons reaction (HWE) reaction. 2,2,2-Trifluoroethanol (Trifluoroethyl alcohol, TFE) is used to study the conformational states of proteins and the folding refolding processes of proteins.

Technology Process of 2,2,2-Trifluoroethanol

There total 238 articles about 2,2,2-Trifluoroethanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

benzyl trifluoroacetate (351-70-2) → 2,2,2-trifluoroethanol (75-89-8) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With trans-[(2,6-bis(di-tert-butylphosphinomethyl)pyridine)Fe(H)₂(CO)]; hydrogen; sodium methylate; In 1,4-dioxane; at 40 ℃; for 16h; under 18751.9 Torr; Glovebox; Inert atmosphere;

DOI:10.1002/anie.201311221

Reference yield: 96.0%

1-isopropenyl-4-nitro-benzene (1830-68-8) → 2,2,2-trifluoroethanol (75-89-8) + 2,2,2-Trifluoroacetaldehyde (75-90-1) + (4-nitrophenyl)ethanone (100-19-6)

Guidance literature:

With Togni's reagent; C₁₄H₁₆Br₂NO₅V; In acetone; for 144h;

Reference yield: 96.0%

Togni's reagent (887144-97-0) + 1-isopropenyl-4-nitro-benzene (1830-68-8) → 2,2,2-trifluoroethanol (75-89-8) + 2,2,2-Trifluoroacetaldehyde (75-90-1) + (4-nitrophenyl)ethanone (100-19-6)

Guidance literature:

With oxygen; C₁₄H₁₆Br₂NO₅V; In acetone; for 144h;

upstream raw materials:

trifluoracetyl chloride

1,1,1-trifluoro-2-chloroethane

2,2,2-trifluoroacetamide

n-butyl trifluoroacetate

Downstream raw materials:

2,2,2-trifluoroethyl methyl ether

(1,1-difluoro-ethyl)-(2,2,2-trifluoro-ethyl)-ether

1,1,2,2-Tetrafluoro-1-(2,2,2-trifluoroethoxy)-ethane

3-nitrophenylcarbamic acid 2,2,2-trifluoroethyl ester

Refernces

• 1、 Kolomnikova,G.D. et al.. "". . . Retrieved 1978.
• 2、 -. "METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND". Paragraph 0071; 0074. . Retrieved 2021/07/10.
• 3、 -. "METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND". Paragraph 0053-0054; 0062-0063. . Retrieved 2021/03/19.