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inquiryProduct Name: 2-(Trifluoromethyl)pyridine Synonyms: Pyridine, 2-(trifluoromethyl)-;ALPHA,ALPHA,ALPHA-TRIFLUORO-2-PICOLINE;2-(TRIFLUOROMETHYL)PYRIDINE;à,à,à-trifluoro-2-picoline;α,α,α-trifluoro-2-picolin
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inquiryProduct Name: 2-(Trifluoromethyl)pyridine Synonyms: Pyridine, 2-(trifluoromethyl)-;ALPHA,ALPHA,ALPHA-TRIFLUORO-2-PICOLINE;à,à,à-trifluoro-2-picoline;α,α,α-trifluoro-2-picoline;2-(TRIFLUOROMETHYL)PYRIDINE;2
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2-bromo-pyridine
(trifluoromethyl)trimethylsilane
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
Stage #1: (trifluoromethyl)trimethylsilane With silver fluoride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: With copper In N,N-dimethyl-formamide for 4h; Stage #3: 2-bromo-pyridine In N,N-dimethyl-formamide at 90℃; for 5h; | 79% |
Conditions | Yield |
---|---|
With copper In N,N-dimethyl-formamide at 0 - 80℃; for 4h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With potassium carbonate; copper(l) chloride at 60℃; for 48h; Inert atmosphere; | 57% |
With copper(l) iodide; 4,4'-Dimethoxy-2,2'-bipyridin; potassium carbonate In benzonitrile at 90℃; for 48h; | 80 %Spectr. |
2-bromo-pyridine
trifluoroacetic acid-methyl ester
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With cesium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 180℃; for 8h; | 45% |
2-iodopyridine
(trifluoromethyl)trimethylsilane
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With potassium fluoride; copper(l) iodide In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide at 25℃; for 6h; | 68% |
2-bromo-pyridine
methyl 3-oxa-ω-fluorosulfonylperfluoropentanoate
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With copper(l) iodide In N,N-dimethyl-formamide at 120℃; for 8h; | 70% |
Conditions | Yield |
---|---|
With triethylamine tris(hydrogen fluoride) In N,N-dimethyl-formamide at 80℃; for 8h; Inert atmosphere; | 90 %Spectr. |
With triethylamine tris(hydrogen fluoride) In N,N-dimethyl-formamide at 80℃; for 20h; | 57 %Spectr. |
2-chloropyridine
methyl 3-oxa-ω-fluorosulfonylperfluoropentanoate
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With copper(l) iodide In N,N-dimethyl-formamide at 120℃; for 8h; | 64% |
2-chloro-6-trifluoromethylpyridine
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With N,N-dimethyl-ethanamine; hydrogen; palladium on activated charcoal In acetic acid methyl ester for 1.5h; |
Conditions | Yield |
---|---|
With copper(l) iodide In N,N-dimethyl-formamide at 45℃; for 8h; | 52% |
2-chloro-6-trifluoromethylpyridine
Diethyl methylmalonate
A
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With potassium tert-butylate In ammonia at -78℃; for 4h; Irradiation; | A n/a B 44% |
Conditions | Yield |
---|---|
With copper In N,N-dimethyl-formamide Inert atmosphere; | 99% |
6,6,6-trifluoro-1-ethoxy-1,3-hexadien-5-one
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With ammonium carbonate at 90 - 130℃; | 62% |
Conditions | Yield |
---|---|
With copper In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; | 80 %Spectr. |
Conditions | Yield |
---|---|
With cesium fluoride; sodium hydroxide In N,N-dimethyl-formamide at 75℃; for 3h; Inert atmosphere; Sealed tube; | 97 %Spectr. |
2-bromo-pyridine
sodium 2,2,2-trifluoroacetate
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With copper(l) iodide In various solvent(s) at 60℃; for 4h; | 41 % Chromat. |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 80℃; for 8h; Sealed tube; Inert atmosphere; | 94 %Spectr. |
3,4-(methylenedioxy)-benzeneboronic acid
B
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With palladium diacetate In ethanol at 30℃; for 24h; Inert atmosphere; | A 7% B n/a |
2-(methylthio)propionic acid
5-bromo-2(trifluoromethyl)pyridine
B
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With (1,2-dimethoxyethane)dichloronickel(II); [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; caesium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl acetamide for 17h; Solvent; Reagent/catalyst; Inert atmosphere; Sealed tube; Irradiation; | A 70% B n/a C n/a |
Conditions | Yield |
---|---|
With ISOPROPYLAMIDE; copper | 74% |
Conditions | Yield |
---|---|
With copper In N,N-dimethyl acetamide at 100℃; for 8h; | 13 % Chromat. |
2-iodopyridine
tris(triphenylphosphane)(trifluoromethyl)copper(I)
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 80℃; | 75 %Spectr. |
Conditions | Yield |
---|---|
Stage #1: trifluoromethan With fluorobenzene; potassium tert-butylate; copper(l) chloride In N,N-dimethyl-formamide for 0.25h; Inert atmosphere; Stage #2: With triethylamine tris(hydrogen fluoride) In N,N-dimethyl-formamide Inert atmosphere; Stage #3: 2-bromo-pyridine In N,N-dimethyl-formamide at 50℃; for 16h; Inert atmosphere; | 30 %Spectr. |
Conditions | Yield |
---|---|
Stage #1: trifluoromethan With fluorobenzene; potassium tert-butylate; copper(l) chloride In N,N-dimethyl-formamide for 0.25h; Inert atmosphere; Stage #2: With triethylamine tris(hydrogen fluoride) In N,N-dimethyl-formamide Inert atmosphere; Stage #3: 2-iodopyridine In N,N-dimethyl-formamide at 50℃; for 16h; Inert atmosphere; | 99 %Spectr. |
Conditions | Yield |
---|---|
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(l) iodide at 50℃; for 24h; Inert atmosphere; | 85 %Spectr. |
2-iodopyridine
iodotrifluoromethane
zinc
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
Stage #1: iodotrifluoromethane; zinc With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone at 20℃; for 2h; Inert atmosphere; Stage #2: 2-iodopyridine With copper(l) iodide at 50℃; for 24h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; chemoselective reaction; | 96 %Spectr. |
Conditions | Yield |
---|---|
at 475℃; | |
at 400℃; | |
at 350 - 520℃; Kinetics; in der Gasphase; |
2-chloropyridine
dibromodifluoromethane
A
2-heptafluoropropyl-pyridine
B
2-(pentafluoroethyl)pyridine
C
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With ISOPROPYLAMIDE; copper at 100℃; for 8h; | A n/a B 23% C 13% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 50℃; for 24h; | 93 %Spectr. |
pyridine
Bromotrifluoromethane
A
4-trifluoromethylpyridine
B
3-(trifluoromethyl)pyridine
C
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; sodium dithionite In water at 65℃; under 2250.2 - 3750.3 Torr; for 2h; | A 5% B 1% C 4% |
2-(trifluoromethyl)pyridine
3-hydroxy-2-trifluoromethylpyridine
Conditions | Yield |
---|---|
Stage #1: 2-(trifluoromethyl)pyridine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 16h; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane for 2h; Stage #3: With peracetic acid In tetrahydrofuran; hexane; water; acetic acid at 0℃; for 1h; | 72% |
Stage #1: 2-(trifluoromethyl)pyridine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 16h; Inert atmosphere; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #3: With peracetic acid In tetrahydrofuran; hexane; acetic acid at -78 - 0℃; for 1h; Inert atmosphere; regioselective reaction; | 72% |
Stage #1: 2-(trifluoromethyl)pyridine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran at -78 - -70℃; for 2h; Stage #2: With Trimethyl borate In tetrahydrofuran at -70℃; for 2h; Stage #3: With dihydrogen peroxide In tetrahydrofuran at -70 - 0℃; for 1h; | 67% |
2-(trifluoromethyl)pyridine
2-(trifluoro-methyl)pyridine 1-oxide
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 72h; | 47% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 24h; | 47% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 24℃; for 12h; Inert atmosphere; | 41% |
2-(trifluoromethyl)pyridine
3-iodo-2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; iodine In tetrahydrofuran; hexane at -75℃; for 2h; | 89% |
Stage #1: 2-(trifluoromethyl)pyridine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Cooling with acetone-dry ice; Stage #2: With iodine In tetrahydrofuran; hexane at -78 - 20℃; | 68% |
tert-butyl 3,3-difluoro-4-methylidene-2-oxopyrrolidine-1-carboxylate
2-(trifluoromethyl)pyridine
tert-butyl {3,3-difluoro-2-methylene-4-oxo-4-[2-(trifluoromethyl)pyridin-3-yl]butyl}carbamate
Conditions | Yield |
---|---|
Stage #1: 2-(trifluoromethyl)pyridine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2.75h; Stage #2: tert-butyl 3,3-difluoro-4-methylidene-2-oxopyrrolidine-1-carboxylate In tetrahydrofuran; hexane at -78℃; for 2h; Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane | 87% |
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; platinum(IV) oxide In water; acetic acid under 2068.65 Torr; for 72h; | |
With hydrogenchloride; hydrogen; platinum(IV) oxide In water; acetic acid under 2068.65 Torr; for 72h; | |
With hydrogenchloride; hydrogen; platinum(IV) oxide In water; acetic acid under 2068.65 Torr; for 72h; |
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With [Rh(cod)(CI)(CAACMe2)]; hydrogen In hexane at 40℃; for 24h; Molecular sieve; diastereoselective reaction; | 70% |
With [Rh(cod)(CI)(CAACMe2)]; hydrogen In hexane at 50℃; under 45004.5 Torr; for 24h; Molecular sieve; | |
With methanesulfonic acid; hydrogen; [(E)-4-methoxy-N-(1-(4-methoxyphenyl)ethylidene)aniline]iridium(III) mesylate In isopropyl alcohol at 50℃; under 37503.8 Torr; for 16h; Autoclave; |
carbon dioxide
2-(trifluoromethyl)pyridine
6-(trifluoromethyl)pyridine-2-carboxylic acid
Conditions | Yield |
---|---|
With n-butyllithium; 2-(N,N-dimethylamino)ethanol In diethyl ether; hexane at -75℃; for 2h; | 71% |
Stage #1: 2-(trifluoromethyl)pyridine With n-butyllithium; 2-(N,N-dimethylamino)ethanol In diethyl ether; hexane at -65℃; Inert atmosphere; Stage #2: carbon dioxide In diethyl ether; hexane at -65 - 50℃; Inert atmosphere; | |
Stage #1: 2-(trifluoromethyl)pyridine With n-butyllithium In diethyl ether; hexane at -65℃; Inert atmosphere; Stage #2: carbon dioxide In diethyl ether; hexane at 0 - 5℃; |
2-(trifluoromethyl)pyridine
3‐(methoxycarbonyl)bicyclo[1.1.1]pentane‐1‐carboxylic acid
Conditions | Yield |
---|---|
With sodium persulfate; sulfuric acid; silver nitrate In water; acetonitrile at 80℃; for 2h; | 5% |
2-(trifluoromethyl)pyridine
trimethylsilyl bis(trifluoromethanesulfonyl)imide
tris-(o-tolyl)phosphine
Conditions | Yield |
---|---|
With tris(pentafluorophenyl)borate In 1,2-dichloro-benzene at 150℃; for 40h; Inert atmosphere; | 64% |
2-(N,N-dimethylamino)ethanol
2-(trifluoromethyl)pyridine
6-(trifluoromethyl)pyridine-2-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: 2-(N,N-dimethylamino)ethanol With n-butyllithium In diethyl ether; hexane at -75 - -65℃; for 0.166667h; Inert atmosphere; Stage #2: 2-(trifluoromethyl)pyridine In diethyl ether; hexane at -65℃; Inert atmosphere; |
Conditions | Yield |
---|---|
Stage #1: 2-(trifluoromethyl)pyridine With n-butyllithium In diethyl ether; hexane; toluene at -100℃; for 0.7h; Inert atmosphere; Stage #2: Triisopropyl borate In diethyl ether; hexane; toluene at -70℃; for 4h; Inert atmosphere; Stage #3: isopropyl alcohol In diethyl ether; hexane; toluene for 2.5h; Inert atmosphere; |
carbon dioxide
2-(trifluoromethyl)pyridine
2-(trifluoromethyl)nicotinic acid
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethylpiperidinyl-lithium at -78℃; for 6h; Large scale reaction; | 77% |
With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -75℃; for 6h; | 73% |
2-(trifluoromethyl)pyridine
2-(trifluoromethyl)pyridin-4-amine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: H2O2, acetic acid 2: 89 percent / H2 / 10percent Pd/C / aq. ethanol / 0.75 h / 1810.02 Torr View Scheme | |
Multi-step reaction with 3 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 25 °C 2: sulfuric acid; nitric acid / 4 h / 0 - 125 °C 3: hydrogen / palladium 10% on activated carbon / 12 h View Scheme | |
Multi-step reaction with 3 steps 1.1: dihydrogen peroxide; acetic acid / water / 12 h / 20 - 70 °C 1.2: pH 7 2.1: sulfuric acid; nitric acid / 2 h / 0 - 130 °C 2.2: pH 7 3.1: hydrogen / palladium 10% on activated carbon / ethanol / 3 h / 20 °C / 1551.49 Torr / Inert atmosphere View Scheme |
2-(trifluoromethyl)pyridine
mesitylenesulfonylhydroxylamine
1-amino-2-trifluoromethylpyridinium mesitylenesulfonate
Conditions | Yield |
---|---|
In chloroform at 20℃; for 108h; |
Conditions | Yield |
---|---|
With Cyclohexanethiol; 10-(naphthalen-1-yl)-10H-phenothiazine; sodium formate In water; dimethyl sulfoxide at 23℃; for 24h; Irradiation; Inert atmosphere; Sealed tube; Schlenk technique; | 47% |
With 3,7-di([1,1′-biphenyl]-4-yl)-10-(naphthalen-1-yl)-10H-phenoxazine; potassium formate; thiophenol In dimethyl sulfoxide at 23℃; for 24h; Inert atmosphere; Irradiation; Sealed tube; | 43% |
Conditions | Yield |
---|---|
Stage #1: styrene; (dimethoxy)methylsilane With copper diacetate; (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane In tetrahydrofuran-d8 at 20℃; Glovebox; Sealed tube; Stage #2: 2-(trifluoromethyl)pyridine In tetrahydrofuran-d8 at 20℃; for 23.5h; Glovebox; Sealed tube; Overall yield = 12 percentSpectr.; Optical yield = 33.333 percent de; diastereoselective reaction; |
2-(trifluoromethyl)pyridine
dithiocarbonic acid O-ethyl S-(2-(trifluoromethyl)pyridin-4-yl) diester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H2O2, acetic acid 2: 89 percent / H2 / 10percent Pd/C / aq. ethanol / 0.75 h / 1810.02 Torr 3: 1.) NaNO2, conc. H2SO4 / 1.) H2O, 0 deg C, 5 min, 2.) H2O, from 5 deg C to RT View Scheme |
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: H2O2, acetic acid 2: 89 percent / H2 / 10percent Pd/C / aq. ethanol / 0.75 h / 1810.02 Torr 3: 1.) NaNO2, conc. H2SO4 / 1.) H2O, 0 deg C, 5 min, 2.) H2O, from 5 deg C to RT 4: 1.) 1 N KOH, 2.) CuBr, Cu2O / 1.) MeOH, 90 min, 2.) DMA, 90 deg C, 6 h View Scheme |
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: H2O2, acetic acid 2: 89 percent / H2 / 10percent Pd/C / aq. ethanol / 0.75 h / 1810.02 Torr 3: 1.) NaNO2, conc. H2SO4 / 1.) H2O, 0 deg C, 5 min, 2.) H2O, from 5 deg C to RT 4: 1.) 1 N KOH, 2.) CuBr, Cu2O / 1.) MeOH, 90 min, 2.) DMA, 90 deg C, 6 h View Scheme |
2-(trifluoromethyl)pyridine
A
2-(difluoromethyl)pyridine
Conditions | Yield |
---|---|
With 3,7-di([1,1′-biphenyl]-4-yl)-10-(naphthalen-1-yl)-10H-phenoxazine; cesium formate In dimethyl sulfoxide at 23℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation; Sealed tube; | A 58% B n/a |
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