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

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

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

• 354-32-5 trifluoracetyl chloride 
• 75-88-7 1,1,1-trifluoro-2-chloroethane 
• 354-38-1 2,2,2-trifluoroacetamide 
• 367-64-6 n-butyl trifluoroacetate 
• 351-70-2 benzyl trifluoroacetate 
• 76-05-1 trifluoroacetic acid 
• 407-25-0 trifluoroacetic anhydride 
• 29817-35-4 1-acetyl-2-methylhydrazine 
• 1118-45-2 2,2,2-Trifluoroethyl cyanate 
• 67-56-1 methanol 
• 94670-31-2 1-(4-methoxyphenyl)ethyl trifluoroethyl ether 
• 77989-23-2 3-Methyl-5-(2,2,2-trifluoro-ethoxy)-1,4,6,9-tetraoxa-5λ⁵-phospha-spiro[4.4]nonan-2-one 
• 94670-29-8 1-(4-(dimethylamino)phenyl)ethyl trifluoroethyl ether 
• 94670-32-3 1-(3-bromo-4-methoxyphenyl)ethyl 2,2,2-trifluoroethyl ether 

Downstream Products

• 2358-54-5 2,2,2-trifluoroethoxyethanol 
• 460-43-5 2,2,2-trifluoroethyl methyl ether 
• 653-96-3 anthranilic acid-(2,2,2-trifluoro-ethyl ester) 
• 2925-42-0 1-butoxy-1-(2,2,2-trifluoro-ethoxy)-ethane 
• 352-28-3 bis(2,2,2-trifluoroethyl) fumarate 
• 25352-91-4 (1,1-difluoro-ethyl)-(2,2,2-trifluoro-ethyl)-ether 
• 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 

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Method for oxidative cracking of compound containing unsaturated double bonds

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METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method comprises the following step: (A) providing a compound (I) with an unsaturated double bond, a reagent with trifluoromethyl, and a catalyst; wherein the catalyst is represented by the following formula (II): M(O)mL1yL2z (II); wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and (B) mixing the compound with an unsaturated double bond and the reagent with a trifluoromethyl to perform an oxidation of the compound with the unsaturated double bond by using the catalyst at air or an oxygen condition to get a compound presented as formula (III):

METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method includes the steps of: (A) providing a compound (I) with an unsaturated double bond, a trifluoromethyl-containing reagent, and a catalyst; wherein, the catalyst is represented by Formula (II): M(O)mL1yL2z??(II);wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and(B) mixing the compound with an unsaturated double bond and the trifluoromethyl-containing reagent to perform an oxidative cleavage of the compound with the unsaturated double bond by using the catalyst in air or under oxygen atmosphere condition to obtain a compound represented by Formula (III):

Transition Metal-Free Direct Hydrogenation of Esters via a Frustrated Lewis Pair

"Frustrated Lewis pairs"(FLPs) continue to exhibit unique reactivity for the reduction of organic substrates, yet to date, the catalytic hydrogenation of an ester functionality has not been demonstrated. Here, we report that iPr3SnNTf2 (1-NTf2; Tf = SO2CF3) is a more potent Lewis acid than the previously studied iPr3SnOTf; in an FLP with 2,4,6-collidine/2,6-lutidine (col/lut), this translates to faster H2 activation and the catalytic hydrogenolysis of an ester bond by a main-group compound, furnishing alcohol and ether (minor) products. The reaction outcome is sensitive to the steric and electronic properties of the substrate; CF3CO2Et and simple formates (HCO2Me and HCO2Et) are catalytically reduced, whereas related esters CF3CO2nBu and CH3CO2Et show only stoichiometric reactivity. A computational case study on the hydrogenation of CF3CO2Et and CH3CO2Et reveals that both share a common mechanistic pathway; however, key differences in the energies of a Sn-acetal intermediate and transition states emerge, favoring CF3CO2Et reduction. The alcohol products reversibly inhibit 1-NTf2/lut via formation of resting-state species 1-OR/[1·(1-OR)]+[NTf2]- however, the extra energy required to regenerate 1-NTf2/lut exacerbates the unfavorable reduction energy profile for CH3CO2Et, ultimately preventing turnover. These findings will assist the design of future main-group catalysts for ester hydrogenation, with improved performance.

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Engineering Catalysts for Selective Ester Hydrogenation

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