75-89-8

Basic information

• Product Name: 2,2,2-Trifluoroethanol
• Synonyms: ,2,2-Trifluoroethyl alcohol;2(3H)-Benzofuranone, 5-hydroxy-;5-Hydroxy-3H-1-benzofuran-2-one;b,b,b-Trifluoroethyl alcohol;2,2,2-TRIFLUOROETHANOL, 99.8%, EXTRA PURE;2,2,2-Trifluoroethanol, extra pure;Trifluoro Ethanol(L);2,2,2-Trifluoroethanol,Trifluoroethyl alcohol
• CAS NO: 75-89-8
• Molecular Formula: C₂H₃F₃O
• Molecular Weight: 100.04
• EINECS: 200-913-6
• Product Categories: organofluorine compounds;Organics;API intermediates;Other Reagents;Fluorinated Building Blocks;Fluorinating Reagents & Building Blocks for Fluorinated Biochemical Compounds;Synthetic Organic Chemistry;Chemistry
• Mol File: 75-89-8.mol
• Article Data: 103

Chemical Properties

• Melting Point: −44 °C(lit.)
• Boiling Point: 77-80 °C(lit.)
• Flash Point: 85 °F
• Appearance: Clear colorless/Liquid
• Density: 1.391 g/mL at 20 °C
• Vapor Density: 3.5 (vs air)
• Vapor Pressure: 70 mm Hg ( 25 °C)
• Refractive Index: n20/D 1.3(lit.)
• Storage Temp.: Store at RT.
• PKA: 12.4(at 25℃)
• Explosive Limit: 8.4-28.8%(V)
• Water Solubility: Miscible with water, ethers, ketones, alcohols and chloroform.
• Stability: Stable. Flammable - note wide explosion limits. Moisture sensitive. Incompatible with strong oxidizing agents, strong acids, sod
• Merck: 14,9682
• BRN: 1733203
• CAS DataBase Reference: 2,2,2-Trifluoroethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-Trifluoroethanol(75-89-8)
• EPA Substance Registry System: 2,2,2-Trifluoroethanol(75-89-8)

Safety Data

• 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
• RIDADR: UN 1986 3/PG 3
• WGK Germany: 1
• RTECS: KM5250000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 75-89-8(Hazardous Substances Data)

Usage

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.

Chemical properties

Boiling point is 73.6℃, melting point is-43.5℃, refractive index is 1.2940, density (25 ℃) is 1.383g/cm3, enthalpy of evaporation is 37.8kJ/mol.

Uses

Different sources of media describe the Uses of 75-89-8 differently. You can refer to the following data:
1. (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.
2. 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.
3. 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.
4. 2,2,2-Trifluoroethanol (Trifluoroethyl alcohol, TFE) is used to study the conformational states of proteins and the folding refolding processes of proteins.

Preparation method

Since 1933 Swarts used trifluoroacetic anhydride as raw material, catalytic reduction method was used to get trichloroethanol, we have developed a series of synthetic methods. According to the type, the reaction can be divided into three kinds: oxidation, reduction and hydrolysis. According to raw material, it can be divided trifluoroacetic acid method, trifluoroacetyl chloride method, trifluoroacetic anhydride method, trifluoroacetate law, trifluoroacetic acetaldehyde, polyvinylidene fluoride method, trifluoroethane (HFC-143a) method and trifluoro chloroethane (HCFC-133a) method.

Hazards & Safety Information

Category: Flammable liquid Toxicity grading: highly toxic Acute oral toxicity-rat LD50: 240 mg/kg; Oral-Mouse LD50: 366 mg/kg Irritation data: Skin-Rabbit 0.75 mg/24 hours and severe; Eyes-rabbit 20 mg/24 hr mild Flammability hazard characteristics: When meets fire, heat, oxidants, it is flammable; it can burn and generate toxic fluoride fumes. Storage characteristics: Treasury ventilation low-temperature drying; it should be stored separately with oxidants. Extinguishing agent: Dry powder, dry sand, carbon dioxide, foam, 1211 fire extinguishing agent.

Chemical Properties

Colorless liquid

Safety Profile

Poison by ingestion, intravenous, and intraperitoneal routes. Moderately toxic by inhalation and skin contact. Experimental reproductive effects. A severe skin and eye irritant. When heated to decomposition it emits toxic fumes of F-.

Purification Methods

Dry it with CaSO4 and a little NaHCO3 (to remove traces of acid) and distil it. Highly TOXIC vapour. [Beilstein 1 IV 1370.]

InChI:InChI=1/C2H3F3O/c3-2(4,5)1-6/h6H,1H2

Synthetic route

n-butyl trifluoroacetate (367-64-6) → 2,2,2-trifluoroethanol (75-89-8)

Conditions	Yield
With trans-[(2,6-bis(di-tert-butylphosphinomethyl)pyridine)Fe(H)2(CO)]; potassium tert-butylate; hydrogen In 1,4-dioxane at 40℃; under 7500.75 Torr; for 16h; Time; Concentration; Pressure; Temperature; Glovebox; Inert atmosphere;	99%
With lithium aluminium tetrahydride; diethyl ether

trifluoroacetic acid-methyl ester (431-47-0) → 2,2,2-trifluoroethanol (75-89-8)

Conditions	Yield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); hydrogen; sodium methylate In methanol at 60℃; under 22502.3 Torr; for 2h; Pressure; Temperature; Time; Concentration; Reagent/catalyst; Autoclave;	99%
With hydrogen; phosphan
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); hydrogen; sodium methylate In methanol at 40℃; under 19001.3 Torr; for 24h; Autoclave; Inert atmosphere;	98 %Spectr.
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); hydrogen; sodium methylate In methanol at 40℃; under 18751.9 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Autoclave;	92 %Spectr.
With C46H43N7OPRu(1+)*BF4(1-); potassium tert-butylate; hydrogen In 1,4-dioxane at 100℃; under 37503.8 Torr; for 2h; Inert atmosphere; Autoclave;	100 %Spectr.

(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-n-decyl)trifluoroacetate (117068-31-2) → 2,2,2-trifluoroethanol (75-89-8) + 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decanol (678-39-7)

Conditions	Yield
With trans-[(2,6-bis(di-tert-butylphosphinomethyl)pyridine)Fe(H)2(CO)]; hydrogen; sodium methylate In 1,4-dioxane at 40℃; under 18751.9 Torr; for 16h; Glovebox; Inert atmosphere;	A 99% B n/a

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

Conditions	Yield
With trans-[(2,6-bis(di-tert-butylphosphinomethyl)pyridine)Fe(H)2(CO)]; hydrogen; sodium methylate In 1,4-dioxane at 40℃; under 18751.9 Torr; for 16h; Glovebox; Inert atmosphere;	A 99% B n/a
With trimethylamine-N-oxide; tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; hydrogen In toluene at 90℃; under 52505.3 Torr; for 17h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere; Glovebox;
With C21H35BrMnN2O2P; hydrogen; potassium hydride; 1,3,5-trimethyl-benzene In toluene at 100℃; under 15001.5 Torr; for 28h; Autoclave; Inert atmosphere;	A 78 %Spectr. B 99 %Spectr.
With C21H35BrMnN2O2P; hydrogen; potassium hydride In toluene at 100℃; under 15001.5 Torr; for 28h;	A 78 %Spectr. B 99 %Spectr.

4-methylbenzyl trifluoroacetate (1524-14-7) → 2,2,2-trifluoroethanol (75-89-8) + 4-Methylbenzyl alcohol (589-18-4)

Conditions	Yield
With trans-[(2,6-bis(di-tert-butylphosphinomethyl)pyridine)Fe(H)2(CO)]; hydrogen; sodium methylate In 1,4-dioxane at 40℃; under 18751.9 Torr; for 16h; Glovebox; Inert atmosphere;	A 99% B n/a

4-(trifluoromethyl)benzyl trifluoroacetate (681035-98-3) → 4-(trifluoromethyl)benzylic alcohol (349-95-1) + 2,2,2-trifluoroethanol (75-89-8)

Conditions	Yield
With trans-[(2,6-bis(di-tert-butylphosphinomethyl)pyridine)Fe(H)2(CO)]; hydrogen; sodium methylate In 1,4-dioxane at 40℃; under 18751.9 Torr; for 16h; Glovebox; Inert atmosphere;	A n/a B 99%

4-fluorobenzyl trifluoroacetate (139058-95-0) → 4-fluorobenzylic alcohol (459-56-3) + 2,2,2-trifluoroethanol (75-89-8)

Conditions	Yield
With trans-[(2,6-bis(di-tert-butylphosphinomethyl)pyridine)Fe(H)2(CO)]; hydrogen; sodium methylate In 1,4-dioxane at 40℃; under 18751.9 Torr; for 16h; Glovebox; Inert atmosphere;	A n/a B 97%
With trimethylamine-N-oxide; tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; hydrogen; triethylamine In toluene at 90℃; under 52505.3 Torr; for 17h; Inert atmosphere; Glovebox;

1,1,1-trifluoro-2-chloroethane (75-88-7) → 2,2,2-trifluoroethanol (75-89-8)

Conditions	Yield
With potassium γ-hydroxybutyrate In 4-butanolide at 200℃; under 11251.1 Torr; for 6h;	96%
With 4-butanolide; potassium hydroxide at 200℃; under 11251.1 Torr; for 6h;	68%
With potassium acetate; ethylene glycol; acetic acid

cyclohexylmethyl trifluoroacetate (164071-20-9) → 2,2,2-trifluoroethanol (75-89-8) + cyclohexylmethyl alcohol (100-49-2)

Conditions	Yield
With trans-[(2,6-bis(di-tert-butylphosphinomethyl)pyridine)Fe(H)2(CO)]; hydrogen; sodium methylate In 1,4-dioxane at 40℃; under 18751.9 Torr; for 48h; Glovebox; Inert atmosphere;	A 95% B n/a
With trimethylamine-N-oxide; tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; hydrogen In toluene at 110℃; under 52505.3 Torr; for 17h; Catalytic behavior; Solvent; Temperature; Inert atmosphere; Glovebox;

allyl trifluoroacetate (383-67-5) → 2,2,2-trifluoroethanol (75-89-8) + allyl alcohol (107-18-6)

Conditions	Yield
With trans-[(2,6-bis(di-tert-butylphosphinomethyl)pyridine)Fe(H)2(CO)]; hydrogen; sodium methylate In 1,4-dioxane at 40℃; under 18751.9 Torr; for 16h; Glovebox; Inert atmosphere;	A 95% B n/a
With trimethylamine-N-oxide; tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; hydrogen; triethylamine In toluene at 90℃; under 52505.3 Torr; for 17h; Inert atmosphere; Glovebox;
With C21H35BrMnN2O2P; hydrogen; potassium hydride; 1,3,5-trimethyl-benzene In toluene at 100℃; under 15001.5 Torr; for 60h; Autoclave; Inert atmosphere;	A 97 %Spectr. B 96 %Spectr.
With C21H35BrMnN2O2P; hydrogen; potassium hydride In toluene at 100℃; under 15001.5 Torr; for 60h;	A 97 %Spectr. B 96 %Spectr.

1,1,1-trifluoroethyl fluorosulfite (75988-14-6) → 2,2,2-trifluoroethanol (75-89-8)

Conditions	Yield
With water at 100℃; autoclave;	93%

trifluoroacetic acid-methyl ester (431-47-0) → 2,2,2-trifluoroethanol (75-89-8) + 2,2,2-trifluoro-1-methoxy-ethanol (431-46-9)

Conditions	Yield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); hydrogen; sodium methylate In methanol at 40℃; under 4500.45 Torr; for 19h; Pressure; Temperature; Time; Concentration; Reagent/catalyst; Autoclave;	A 7% B 93%
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); hydrogen; sodium methylate In methanol at 40℃; under 15201 Torr; for 6h; Autoclave; Inert atmosphere;
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); hydrogen; sodium methylate In methanol at 40℃; under 7600.51 Torr; for 6h; Autoclave; Inert atmosphere;

tris(2,2,2-trifluoroethyl)phosphite (370-69-4) + 2,2,3,3,4,4,5,5-octafluorovaleraldehyde (2648-47-7) → 2,2,2-trifluoroethanol (75-89-8) + bis(2,2,2-trifluoroethyl) (1H,5H-octafluoro-1-hydroxypentyl)phosphonate

Conditions	Yield
In benzene at 20 - 25℃; for 2h;	A n/a B 89%

trifluoroacetic acid-methyl ester (431-47-0) → methanol (67-56-1) + 2,2,2-trifluoroethanol (75-89-8)

Conditions	Yield
With hydrogen; <(Ph3P)(Ph2P)RuH2-K+*diglyme>2 In toluene at 90℃; under 4650.4 Torr; for 20h; Title compound not separated from byproducts;	A n/a B 88%
With (K(1+))2<(Ph3P)3(Ph2P)Ru2H4>(2-)*2C6H14O3; hydrogen In toluene at 90℃; under 4650.4 Torr; for 20h;

trifluoroacetic anhydride (407-25-0) → 2,2,2-trifluoroethanol (75-89-8)

Conditions	Yield
With [Zn(BH4)2(py)] In tetrahydrofuran for 1h; Heating;	85%
With lithium aluminium tetrahydride; diethyl ether
With platinum Hydrogenation.unter Druck und anschliessenden Behandeln mit Eiswasser;

methyl(2,2,2-trifluoro-ethoxo){1,2-bis(diphenylphosphino)ethane}palladium (115981-45-8) → methane (34557-54-5) + ethane (74-84-0) + 2,2,2-trifluoroethanol (75-89-8)

Conditions	Yield
In further solvent(s) Thermolysis (120°C) of starting complex (diphenylmethane, vac.).; GLC.;	A 11% B 10% C 84%

but-2-en-1-yl 2,2,2-trifluoroacetate (6864-58-0) → (E/Z)-2-buten-1-ol (6117-91-5) + 2,2,2-trifluoroethanol (75-89-8)

Conditions	Yield
With trans-[(2,6-bis(di-tert-butylphosphinomethyl)pyridine)Fe(H)2(CO)]; hydrogen; sodium methylate In 1,4-dioxane at 40℃; under 18751.9 Torr; for 16h; Glovebox; Inert atmosphere;	A n/a B 84%

2-methoxyethyl trifluoroacetate (41017-81-6) → 2-methoxy-ethanol (109-86-4) + 2,2,2-trifluoroethanol (75-89-8)

Conditions	Yield
With trans-[(2,6-bis(di-tert-butylphosphinomethyl)pyridine)Fe(H)2(CO)]; hydrogen; sodium methylate In 1,4-dioxane at 40℃; under 18751.9 Torr; for 16h; Glovebox; Inert atmosphere;	A n/a B 80%

trifluoroacetic acid 2-phenylethyl ester (55419-66-4) → 2,2,2-trifluoroethanol (75-89-8) + 2-phenylethanol (60-12-8)

Conditions	Yield
With trans-[(2,6-bis(di-tert-butylphosphinomethyl)pyridine)Fe(H)2(CO)]; hydrogen; sodium methylate In 1,4-dioxane at 40℃; under 18751.9 Torr; for 16h; Glovebox; Inert atmosphere;	A 78% B n/a
With trimethylamine-N-oxide; tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; hydrogen In toluene at 90℃; under 52505.3 Torr; for 17h; Inert atmosphere; Glovebox;

isopropyl Trifluoroacetate (400-38-4) → 2,2,2-trifluoroethanol (75-89-8) + isopropyl alcohol (67-63-0)

Conditions	Yield
With trans-[(2,6-bis(di-tert-butylphosphinomethyl)pyridine)Fe(H)2(CO)]; hydrogen; sodium methylate In 1,4-dioxane at 40℃; under 18751.9 Torr; for 60h; Glovebox; Inert atmosphere;	A 77% B n/a
With trimethylamine-N-oxide; tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; hydrogen; triethylamine In toluene at 90℃; under 52505.3 Torr; for 17h; Inert atmosphere; Glovebox;

n-butyl trifluoroacetate (367-64-6) → 2,2,2-trifluoroethanol (75-89-8) + butan-1-ol (71-36-3)

Conditions	Yield
With trans-[(2,6-bis(di-tert-butylphosphinomethyl)pyridine)Fe(H)2(CO)]; hydrogen; sodium methylate In 1,4-dioxane at 40℃; under 18751.9 Torr; for 16h; Reagent/catalyst; Solvent; Time; Temperature; Glovebox; Inert atmosphere;	A 77% B n/a

2,2,2-Trifluoroethyl cyanate (1118-45-2) + N-benzoyl-N'-benzylhydrazine (1215-52-7) → 2,2,2-trifluoroethanol (75-89-8) + 3-Benzyl-5-phenyl-Δ4-1,3,4-oxadiazolin-2-imin (27643-04-5)

Conditions	Yield
In diethyl ether; ethanol for 1h; Ambient temperature;	A n/a B 75%

1-[tris(trimethylsilyl)silyl]-2,2,2-trifluoroethanol (182255-86-3) → 2,2,2-trifluoroethanol (75-89-8)

Conditions	Yield
With methanol In dichloromethane at 10℃; for 0.5h; Product distribution; Irradiation;	62%
In methanol; dichloromethane desilylation; Photolysis;	62%

glycolic Acid (79-14-1) → 1,1,1,2-tetrafluoroethane (811-97-2) + 2,2,2-trifluoroethanol (75-89-8)

Conditions	Yield
With sulfur tetrafluoride at 160℃; for 8h; autoclave;	A 30% B 48%

glycolic Acid (79-14-1) → 1,1,1,2-tetrafluoroethane (811-97-2) + 2,2,2-trifluoroethanol (75-89-8) + 1,1,1-trifluoroethyl fluorosulfite (75988-14-6)

Conditions	Yield
With sulfur tetrafluoride at 60℃; for 15h; autoclave;	A 26% B 5% C 42%

trifluoracetyl chloride (354-32-5) → 2,2,2-trifluoroethanol (75-89-8)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

2-(2,2-difluoroethoxy)-1,1,1-trifluoroethane → 2,2,2-trifluoroethanol (75-89-8)

Conditions	Yield
beim Aufbewahren;

2,2,2-trifluoroacetamide (354-38-1) → 2,2,2-trifluoroethanol (75-89-8)

Conditions	Yield
With platinum(IV) oxide; diethyl ether at 90℃; Hydrogenation.unter Druck;

benzyl trifluoroacetate (351-70-2) → 2,2,2-trifluoroethanol (75-89-8)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

2,2,2-trifluoroethanol (75-89-8) + p-toluenesulfonyl chloride (98-59-9) → 2,2,2-Trifluoroethyl p-toluenesulfonate (433-06-7)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 18h; Inert atmosphere;	100%
With triethylamine In dichloromethane at 20℃; for 18h;	100%
With triethylamine In chloroform for 6h; Ambient temperature;	98%

3-benzyl-1-methyl-2-oxo-2-phenyl-2λ5-[1,3,2]diazaphospholidin-4-one (64642-21-3) + 2,2,2-trifluoroethanol (75-89-8) → C18H20F3N2O3P

Conditions	Yield
With triethylamine In chloroform for 72h;	100%

2,2,2-trifluoroethanol (75-89-8) + α-t-Butyldimethylsilylbenzyl p-toluenesulfonate (131123-36-9) → tert-Butyl-dimethyl-[phenyl-(2,2,2-trifluoro-ethoxy)-methyl]-silane (134644-20-5)

Conditions	Yield
With 2,6-dimethylpyridine	100%

2,2,2-trifluoroethanol (75-89-8) + 2-(4-methylphenyl)prop-2-en-1-yl 4-toluenesulfonate (89618-93-9) → 2-(4-methylphenyl)-1-(2,2,2-trifluoroethoxy)prop-2-ene (89619-18-1)

Conditions	Yield
With 2,6-dimethylpyridine at 80℃; for 24h;	100%
at 65℃; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.), other temp.;	100%

2,2,2-trifluoroethanol (75-89-8) + 1-chlorocyclopropyl methyl sulfide (78708-99-3) → 1-Methylsulfanyl-1-(2,2,2-trifluoro-ethoxy)-cyclopropane

Conditions	Yield
at 0℃;	100%

2,2,2-trifluoroethanol (75-89-8) + 1-bromocyclopropyl benzyl sulfide (78709-02-1) → [1-(2,2,2-Trifluoro-ethoxy)-cyclopropylsulfanylmethyl]-benzene

Conditions	Yield
at 0℃;	100%

2,2,2-trifluoroethanol (75-89-8) + 1-bromocyclopropyl phenetyl sulfide (78709-15-6) → {2-[1-(2,2,2-Trifluoro-ethoxy)-cyclopropylsulfanyl]-ethyl}-benzene

Conditions	Yield
at 0℃;	100%

2,2,2-trifluoroethanol (75-89-8) + 4-chlorobenzonitrile (100-00-5) → 1-(2,2,2-trifluoroethoxy)-4-nitrobenzene (62149-35-3)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 25℃; for 1h; Inert atmosphere;	100%
Stage #1: 2,2,2-trifluoroethanol With sodium hydride In N,N-dimethyl-formamide Cooling with liquid nitrogen; Stage #2: 4-chlorobenzonitrile In N,N-dimethyl-formamide at 100℃; for 3h; Cooling with liquid nitrogen;	98%
With sodium hydride In N,N-dimethyl-formamide 1.) r.t., 2.) 130 deg C, 10 h;	92%

2,2,2-trifluoroethanol (75-89-8) + phenyl chloroformate (1885-14-9) → 2,2,2-trifluoroethyl phenyl carbonate (152899-11-1)

Conditions	Yield
With pyridine	100%
With pyridine In dichloromethane at 20℃; for 1h;

2,2,2-trifluoroethanol (75-89-8) + N-Cbz-Ala (1142-20-7) → Z-L-Ala 2,2,2-trifluoroethyl ester (203640-41-9)

Conditions	Yield
With pyridine; di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; for 22h;	100%
With Candida antartica lipase B at 50℃; for 16h; Molecular sieve; Enzymatic reaction;	96%
With dmap; triethylamine; dicyclohexyl-carbodiimide In butan-1-ol at 20℃; pH=8 - 9;	63.9%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane

2,2,2-trifluoroethanol (75-89-8) + (Z)-4-benzyloxy-but-2-en-1-ol (81028-03-7) → [2-(2,2,2-trifluoro-ethoxy)-but-3-enyloxymethyl]-benzene (373393-05-6)

Conditions	Yield
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In benzene at 20℃; for 6h; Mitsunobu reaction;	100%

2,2,2-trifluoroethanol (75-89-8) + rac-3-bromocyclohexene (1521-51-3) → 3-(2',2',2'-trifluoroethoxy)-cyclohex-1-ene (373393-06-7)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; tetra-(n-butyl)ammonium iodide	100%
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; tetra-(n-butyl)ammonium iodide at 20℃; for 12h;	71%

2,2,2-trifluoroethanol (75-89-8) + 3-Chloro-2-methylpropene (563-47-3) → 2-methyl-3-(2',2',2'-trifluoroethoxy)-prop-1-ene (74407-77-5)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; tetra-(n-butyl)ammonium iodide	100%
Stage #1: 2,2,2-trifluoroethanol With potassium hydroxide at 40℃; Stage #2: 3-Chloro-2-methylpropene In water at 40℃;	78%
With potassium carbonate In N,N-dimethyl-formamide

2,2,2-trifluoroethanol (75-89-8) + 1-adamantylmethanol → octahydro-2,5-methano-indene-5-carboxylic acid 2,2,2-trifluoro-ethyl ester

Conditions	Yield
With iodine; potassium carbonate at 50℃; for 5h;	100%

2,2,2-trifluoroethanol (75-89-8) + 1-adamantanemethanol (770-71-8) → 2,2,2-trifluoroethyl adamantanecarboxylate

Conditions	Yield
With iodine; potassium carbonate at 50℃; for 5h;	100%

2,2,2-trifluoroethanol (75-89-8) + (E)-4-(benzyloxy)-2-buten-1-ol (80885-30-9, 81028-03-7, 69152-88-1) → 4-(2',2',2'-trifluoroethoxy)-1-benzyloxy-but-2Z-ene (803730-98-5)

Conditions	Yield
Stage #1: (E)-4-(benzyloxy)-2-buten-1-ol With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In benzene at 20℃; for 0.166667h; Stage #2: 2,2,2-trifluoroethanol In benzene at 20℃; for 6h;	100%

2,2,2-trifluoroethanol (75-89-8) + PhCO-X → 2,2,2-trifluoroethyl benzoate (1579-72-2)

Conditions	Yield
With boron trifluoride; toluene at 0℃;	100%

2,2,2-trifluoroethanol (75-89-8) + 5-chloro-4-formyl-1,3-dimethylpyrazole (27006-76-4) → 1,3-dimethyl-5-(2,2,2-trifluoroethoxy)-1H-pyrazole-4-carbaldehyde (126764-32-7)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 3h;	100%

C14H11NO2 (947697-83-8) + 2,2,2-trifluoroethanol (75-89-8) → C16H14F3NO3

Conditions	Yield
silver trifluoromethanesulfonate at 25℃;	100%

2,2,2-trifluoroethanol (75-89-8) + bis(2-fluoro-2,2-dinitroethyl)dichloroformal (113689-58-0) → bis(2-fluoro-2,2-dinitroethyl)bis(2,2,2-trifluoroethyl)orthocarbonate (210754-61-3)

Conditions	Yield
In 1,2-dichloro-ethane	100%

2,2,2-trifluoroethanol (75-89-8) + bromoacetic acid tert-butyl ester (5292-43-3) → tert-butyl 2-(2,2,2-trifluoroethoxy)acetate (252947-89-0)

Conditions	Yield
Stage #1: 2,2,2-trifluoroethanol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.75h; Stage #2: bromoacetic acid tert-butyl ester In tetrahydrofuran at 20℃; for 15h;	100%

2,2,2-trifluoroethanol (75-89-8) + 1,4-bis<(1-imidazolyl)carbonyloxy>-cis-2-butene (1026530-53-9) → (Z)-but-2-ene-1,4-bis(2',2',2'-trifluoroethylcarbonate) (1155875-17-4)

Conditions	Yield
With dmap In dichloromethane at 20℃; Inert atmosphere;	100%

2,2,2-trifluoroethanol (75-89-8) + 2,4-Difluoronitrobenzene (446-35-5) → 4-fluoro-1-nitro-2-(2,2,2-trifluoroethoxy)benzene (186386-91-4)

Conditions	Yield
With sodium hydroxide In toluene at 30 - 50℃; for 16.5h;	100%
With caesium carbonate In tetrahydrofuran at 20℃;	99.8%
With caesium carbonate In tetrahydrofuran at 25℃; for 8h;	67%

2,2,2-trifluoroethanol (75-89-8) + 5,11,17,23,29,35-hexa-tert-butyl-2-chloro-37,38,39,40,41,42-hexamethoxycalix[6]arene (1227410-41-4) → 5,11,17,23,29,35-hexa-tert-butyl-37,38,39,40,41,42-hexamethoxy-2-(2,2,2-trifluoroethoxy)calix[6]arene

Conditions	Yield
In chloroform Reflux;	100%

4-butoxy-2,2-bis-trifluoromethyl-oxetane (17129-00-9) + 2,2,2-trifluoroethanol (75-89-8) → C11H15F9O3 (1226778-13-7)

Conditions	Yield
at 25 - 35℃;	100%

2,2,2-trifluoroethanol (75-89-8) + acrylonitrile (107-13-1) → 3-(2,2,2-trifluoroethoxy)propionitrile (272128-06-0)

Conditions	Yield
With [μN,κP,κC,κN-{2-(i-Pr2PO),6-(CH2NBn)-(C6H3)}Ni]2 In benzene at 20℃; for 5.5h;	100%
With C31H23F3NiO5P2S; triethylamine In toluene at 60℃; for 3h; Inert atmosphere;

2,2,2-trifluoroethanol (75-89-8) + diethyl chlorophosphate (814-49-3) → Diethyl (2,2,2-trifluoroethyl) phosphate

Conditions	Yield
With triethylamine at 20℃; for 5h;	100%

2,2,2-trifluoroethanol (75-89-8) + 2-chloro-4-amino-5-methylpyrimidine (14394-70-8) → 5-methyl-2-(2,2,2-trifluoro-ethoxy)-pyrimidin-4-ylamine (1319068-21-7)

Conditions	Yield
Stage #1: 2,2,2-trifluoroethanol With sodium for 1h; Inert atmosphere; Stage #2: 2-chloro-4-amino-5-methylpyrimidine at 90℃;	100%
Stage #1: 2,2,2-trifluoroethanol With sodium at 20℃; for 1h; Inert atmosphere; Stage #2: 2-chloro-4-amino-5-methylpyrimidine at 90℃;	100%

2,2,2-trifluoroethanol (75-89-8) + 2-Fluoro-5-nitrobenzotrifluoride (400-74-8) → 4-nitro-1-(2,2,2-trifluoroethoxy)-2-(trifluoromethyl)benzene (1324003-80-6)

Conditions	Yield
Stage #1: 2,2,2-trifluoroethanol With sodium hydride In acetonitrile; mineral oil at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 2-Fluoro-5-nitrobenzotrifluoride In acetonitrile; mineral oil for 1h;	100%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; Sealed tube;	87%

2,2,2-trifluoroethanol (75-89-8) + 5,6-dichloronicotinic acid (41667-95-2) → 5-chloro-6-(2,2,2-trifluoroethoxy)nicotinic acid (953729-63-0)

Conditions	Yield
Stage #1: 2,2,2-trifluoroethanol With sodium hydride In N,N-dimethyl acetamide; mineral oil at 0℃; for 0.333333h; Stage #2: 5,6-dichloronicotinic acid In N,N-dimethyl acetamide; mineral oil at 90℃; for 2h;	100%
With potassium hydroxide In dimethyl sulfoxide at 120℃; for 24h;

Upstream product

• 354-38-1 2,2,2-trifluoroacetamide 
• 76-05-1 trifluoroacetic acid 
• 407-25-0 trifluoroacetic anhydride 
• 420-46-2 2,2,2-trifluoroethanol 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 407-38-5 2,2,2-trifluoroethyl trifluoroacetate 
• 1118-45-2 2,2,2-Trifluoroethyl cyanate 
• 1199-86-6 N-(phenylacetyl)-N'-methylhydrazine 
• 32042-38-9 2,2,2-trifluoroethyl formate 
• 93111-30-9 2,2,2-trifluoroethyl picolinate 
• 1215-52-7 N-benzoyl-N'-benzylhydrazine 
• 371-67-5 2,2,2-trifluorodiazoethane 
• 100-51-6 benzyl alcohol 
• 60-29-7 diethyl ether 

Downstream Products

• 2358-54-5 2,2,2-trifluoroethoxyethanol 
• 2925-42-0 1-butoxy-1-(2,2,2-trifluoro-ethoxy)-ethane 
• 352-28-3 bis(2,2,2-trifluoroethyl) fumarate 
• 406-78-0 1,1,2,2-Tetrafluoro-1-(2,2,2-trifluoroethoxy)-ethane 
• 403-99-6 3-nitrophenylcarbamic acid 2,2,2-trifluoroethyl ester 
• 339-46-8 (4-nitro-phenyl)-phosphonic acid mono-(2,2,2-trifluoro-ethyl ester) 
• 732-03-6 diphenyl-(2,2,2-trifluoro-ethoxy)-borane 
• 659-18-7 tris(2,2,2-trifluoroethyl) borate 
• 370-69-4 tris(2,2,2-trifluoroethyl)phosphite 
• 358-63-4 tris(2,2,2-trifluoroethyl) phosphate 
• 407-38-5 2,2,2-trifluoroethyl trifluoroacetate 
• 333-36-8 1,1,1-trifluoro-2-(2,2,2-trifluoroethoxy)ethane 
• 782-94-5 4-chlorophenylcarbamic acid 2,2,2-trifluoroethyl ester 
• 537-83-7 2,2,2-trifluoroethyl p-tolylcarbamate 

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