1-oxido-4-(trifluoromethyl)pyridin-1-ium
4-trifluoromethylpyridine
Conditions | Yield |
---|---|
With phenylsilane; 3-Methyl-1-phenyl-2-phospholene 1-oxide In acetonitrile for 16h; Irradiation; chemoselective reaction; | 93% |
4-iodopyridine
4-trifluoromethylpyridine
Conditions | Yield |
---|---|
With copper In N,N-dimethyl-formamide at 60℃; for 11h; | 91% |
Conditions | Yield |
---|---|
With F6Mo at 170 - 190℃; for 40h; | 80% |
3-hydroxy-3-trifluoromethyl-1,5-pentanedialdehyde
4-trifluoromethylpyridine
Conditions | Yield |
---|---|
With ammonia In methanol for 24h; Heating; | 70% |
With ammonium hydroxide In methanol for 24h; Reflux; | 70% |
2-chloro-4-trifluoromethyl pyridine
4-trifluoromethylpyridine
Conditions | Yield |
---|---|
With propylamine In tetrahydrofuran at 20℃; for 15h; Reagent/catalyst; Solvent; Inert atmosphere; Irradiation; Sealed tube; | 68% |
With triethylamine; Lumogen F Orange 240 In N,N-dimethyl-formamide at 40℃; for 16h; Irradiation; | 91 %Chromat. |
With ZnSe/CdS core/shell QDs; N-ethyl-N,N-diisopropylamine In hexane at 25℃; for 48h; Irradiation; Inert atmosphere; | 23 %Chromat. |
4-iodopyridine
(trifluoromethyl)trimethylsilane
4-trifluoromethylpyridine
Conditions | Yield |
---|---|
With potassium fluoride; copper(l) iodide In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide at 25℃; for 6h; | 25% |
With C13H27CuN2O(1+) In N,N-dimethyl-formamide at 25℃; for 112h; | 99 %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% |
pyridine
iodotrifluoromethane
A
4-trifluoromethylpyridine
B
3-(trifluoromethyl)pyridine
C
3,5-bis(trifluoromethyl)pyridine
D
2,6-bis-(trifluoromethyl)pyridine
E
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
for 96h; Product distribution; Irradiation; The yields, the kind of products depend on the time of the irrad. and/or the temp., and the mol. ratio. Other trifluorometh. agents investigated; |
4-hydroxy-4-trifluoromethyl-1,6-heptadiene
4-trifluoromethylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / O3 / CH2Cl2; methanol / 24 h / -78 °C 2: 70 percent / NH3 / methanol / 24 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1.1: ozone / dichloromethane; methanol / -78 °C 1.2: 2 h / 20 °C 2.1: ammonium hydroxide / methanol / 24 h / Reflux View Scheme |
pyridine
Togni's reagent
A
4-trifluoromethylpyridine
B
3-(trifluoromethyl)pyridine
C
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
In acetonitrile at 80℃; for 96h; Inert atmosphere; | A 3 %Spectr. B 16 %Spectr. C 17 %Spectr. |
Conditions | Yield |
---|---|
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; copper (I) acetate; potassium carbonate In N,N-dimethyl-formamide at 60℃; for 12h; Inert atmosphere; 26 W fluorescent light bulbs; | 64 %Spectr. |
trifluoromethylcopper(I)
4-pyridylboronic acid
4-trifluoromethylpyridine
Conditions | Yield |
---|---|
With oxygen; triethylamine tris(hydrogen fluoride) In N,N-dimethyl-formamide at 25℃; for 4h; | 67 %Spectr. |
trifluoromethylcopper(I)
4-bromopyridine hydrochloride
4-trifluoromethylpyridine
Conditions | Yield |
---|---|
With triethylamine tris(hydrogen fluoride) In N,N-dimethyl-formamide at 23 - 50℃; for 39h; Glovebox; Sealed tube; | 74 %Spectr. |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 100℃; for 8h; Sealed tube; Inert atmosphere; | 75 %Spectr. |
4-iodopyridine
4-trifluoromethylpyridine
Conditions | Yield |
---|---|
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; silver fluoride In N,N-dimethyl-formamide at 100℃; for 2h; Time; Inert atmosphere; Sealed tube; | 83 %Spectr. |
Conditions | Yield |
---|---|
In dichloromethane Kinetics; |
pyridine
A
4-trifluoromethylpyridine
B
3-(trifluoromethyl)pyridine
C
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
In neat (no solvent) at 25℃; Schlenk technique; Inert atmosphere; Glovebox; |
2-bromo-4-(trifluoromethyl)pyridine
4-trifluoromethylpyridine
Conditions | Yield |
---|---|
With ZnSe/CdS core/shell QDs; N-ethyl-N,N-diisopropylamine In hexane at 25℃; for 48h; Irradiation; Inert atmosphere; | 39 %Chromat. |
Conditions | Yield |
---|---|
With dilithium tetrabromocuprate; 1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)-2-trisilanol; Ir(2-(2,4-difluorophenyl)-5-fluoropyridine)2(4,4'-di(trifluoromethyl)-2,2'-bipyridyl)PF6; sodium carbonate In acetone at 35℃; Irradiation; |
pyridine
trifluoroacetic acid
A
4-trifluoromethylpyridine
B
3-(trifluoromethyl)pyridine
C
2-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
In acetonitrile at 20℃; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Electrolysis; Overall yield = 82 %Chromat.; regioselective reaction; |
Conditions | Yield |
---|---|
With potassium fluoride In N,N-dimethyl-formamide at 100℃; for 6h; Inert atmosphere; Schlenk technique; | 36 %Spectr. |
Conditions | Yield |
---|---|
In toluene for 2h; Equilibrium constant; Concentration; Inert atmosphere; |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; |
4-trifluoromethylpyridine
mesitylenesulfonylhydroxylamine
1-amino-4-trifluoromethylpyridinium 2,4,6-trimethylbenzenesulfonate
Conditions | Yield |
---|---|
In dichloromethane at 0 - 20℃; for 18h; | 100% |
In dichloromethane at 0 - 20℃; for 21h; |
4-trifluoromethylpyridine
[Al(η1-allyl)3(4-dimethylaminopyridine)]
[Al(η1-allyl)2(κ-N-2-allyl-4-trifluoromethyl-1,2-dyhydripyridine-1-yl)(4-dimethylaminopyridine)]
Conditions | Yield |
---|---|
In tetrahydrofuran-d8 under Ar, Schlenk technique; soln. of 4-CF3-pyridine in THF-d8 added to soln. of Al complex in THF-d8, react. for 20 h; evapn. under vac., oil dried under vac. for 2 h; elem. anal.; | 99% |
In tetrahydrofuran under Ar, Schlenk technique; Al complex and 4-CF3-pyridine in THF at room temp.; |
4-trifluoromethylpyridine
[Al(η1-allyl)3(triphenylphosphine oxide)]
[Al(η1-allyl)2(κ-N-2-allyl-4-trifluoromethyl-1,2-dyhydripyridine-1-yl)(triphenylphosphine oxide)]
Conditions | Yield |
---|---|
In tetrahydrofuran under Ar, Schlenk technique; addn. of 4-CF3-pyridine to soln. of Al complex in THF, react. for 18 h; evapn. under vac., oil dried under vac. for 2 h; elem. anal.; | 99% |
bis(1,5-cyclooctadiene)diiridium(I) dichloride
4-trifluoromethylpyridine
Conditions | Yield |
---|---|
In dichloromethane react. of Ir complex with NC5H4CF3 (6-10 equiv.) at 23°C for 1 h,then NaB(C6H3(CF3)2)4 (1.2-1.5 equiv.) added, kept for 12 h; | 99% |
4-trifluoromethylpyridine
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 16h; Inert atmosphere; | 99% |
4-trifluoromethylpyridine
Conditions | Yield |
---|---|
In diethyl ether; benzene Inert atmosphere; Glovebox; Schlenk technique; | 99% |
Conditions | Yield |
---|---|
With [Rh(cod)(CI)(CAACMe2)]; hydrogen In hexane at 40℃; for 24h; Molecular sieve; diastereoselective reaction; | 98% |
With hydrogen In tetrahydrofuran at 30℃; under 15001.5 Torr; for 4h; Catalytic behavior; Autoclave; Glovebox; | 49 %Chromat. |
With hydrogen In water; isopropyl alcohol at 120℃; under 37503.8 Torr; for 24h; Autoclave; | 94 %Chromat. |
4-trifluoromethylpyridine
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 2h; | 98% |
4-trifluoromethylpyridine
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)-1,2-dihydropyridine
Conditions | Yield |
---|---|
With [La(η5-C5(CH3)5)H]2 at 25 - 35℃; for 0.4h; | 96% |
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tricyclohexylphosphine In toluene at 50℃; for 24h; Inert atmosphere; | 92% |
With P(C6H11)3; chloro(1,5-cyclooctadiene)rhodium(I) dimer In toluene ligand reacted with pinacolborane in toluene at 50°C for 24 h in presence of (Rh(C8H12)Cl)2 and P(C6H11)3; treated with activated charcoal, filtered under N2, concd. in vacuo; | 92% |
4-trifluoromethylpyridine
bis(trifluoromethanesulfonyl)amide
Conditions | Yield |
---|---|
In dichloromethane at 22 - 26℃; for 0.75h; Inert atmosphere; | 95% |
tetrafluoroboric acid diethyl ether
4-trifluoromethylpyridine
Conditions | Yield |
---|---|
In diethyl ether at 0 - 20℃; | 95% |
4-trifluoromethylpyridine
1-oxido-4-(trifluoromethyl)pyridin-1-ium
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 24h; Inert atmosphere; | 94% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 16h; | 86% |
With 3-chloro-benzenecarboperoxoic acid In chloroform at 0 - 20℃; for 16.8h; | 85% |
diazoacetic acid ethyl ester
N-methylmaleimide
4-trifluoromethylpyridine
Conditions | Yield |
---|---|
With [Fe(tetraphenylporphyrin)Cl] In toluene at 20℃; for 3h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
Stage #1: 4-trifluoromethylpyridine; methyl iodide In acetonitrile at 20℃; Stage #2: With AG(R)21K anion exchange resin chloride form 50-100 mesh Further stages.; | 93% |
Conditions | Yield |
---|---|
Stage #1: 4-trifluoromethylpyridine; iodomethane-d3 at 80℃; Stage #2: With ammonium hexafluorophosphate In water | 92% |
4-trifluoromethylpyridine
1-benzyl-4-(trifluoromethyl)-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 0 - 14℃; for 1.5h; | 92% |
Conditions | Yield |
---|---|
With copper(l) iodide; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With perchloric acid; ethyl o-mesitylsulfonylacetohydroxamic acid; potassium carbonate In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide at 20℃; for 20h; | 92% |
4-trifluoromethylpyridine
benzyl bromide
1-benzyl-4-(trifluoromethyl)pyridin-1-ium bromide
Conditions | Yield |
---|---|
In acetonitrile at 90℃; for 12h; Inert atmosphere; | 91% |
In acetonitrile at 85℃; for 0.25h; Reflux; |
Conditions | Yield |
---|---|
Stage #1: 4-trifluoromethylpyridine; methyl iodide at 80℃; Stage #2: With ammonium hexafluorophosphate In water | 90% |
4-trifluoromethylpyridine
[C2H5NC4H4B(O3SCF3)]
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 4h; Inert atmosphere; | 90% |
In dichloromethane glovebox; soln. of substituted pyridine added to stirred soln. of azaborine, mixt. stirred for 1 h at room temp.; soln. cooled to -20 °C, left at this temp. for 24 h, after crystals pptd. supernatant decanted, solid washed with n-pentane, solvent removed (reduced pressure); | 90% |
Conditions | Yield |
---|---|
Stage #1: 4-trifluoromethylpyridine; α-bromoacetophenone In N,N-dimethyl-formamide at 100℃; Stage #2: ethyl acrylate With sodium acetate; copper(II) acetate monohydrate In N,N-dimethyl-formamide at 100℃; for 16h; | 88.9% |
Conditions | Yield |
---|---|
With C29H38PRuS(1+)*C32H12BF24(1-) In neat (no solvent) at 20℃; for 12h; Inert atmosphere; Glovebox; | 88% |
4-trifluoromethylpyridine
trimethylsilyl trifluoromethanesulfonate
Conditions | Yield |
---|---|
With sulfur dichloride In dichloromethane at -78℃; Inert atmosphere; | 87% |
4-trifluoromethylpyridine
Conditions | Yield |
---|---|
In methanol for 24h; Reflux; | 87% |
Conditions | Yield |
---|---|
In acetonitrile at 80℃; | 87% |
bis(1,5-cyclooctadiene)diiridium(I) dichloride
4-trifluoromethylpyridine
tricyclohexylphosphine
Conditions | Yield |
---|---|
In dichloromethane NC5H4CF3 (1 equiv.) added to soln. of Ir complex (0.5 equiv.) at 23°C, kept for 30 min, Cy3P (1 equiv.) added, after 30 min NaB(C6H3(CF3)2)4 (1.02 equiv.) added, kept for 1 h; concd., chromd. (SiO2, CH2CL2); | 86% |
4-trifluoromethylpyridine
carbon dioxide
4-(trifluoromethyl)nicotinic acid
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at -75℃; for 2h; | 84% |
Molecular Structure:
Molecular Formula: C6H4F3N
Molecular Weight: 147.0979
IUPAC Name: 4-(Trifluoromethyl)pyridine
Synonyms of 4-(Trifluoromethyl)pyridine (CAS NO.3796-24-5): Pyridine, 4-trifluoromethyl-
CAS NO: 3796-24-5
Classification Code: Pyridine series ; Pyridine ; Pyridines ; C6 ; Heterocyclic Building Blocks
Index of Refraction: 1.418
Molar Refractivity: 29.32 cm3
Molar Volume: 116.1 cm3
Surface Tension: 24.5 dyne/cm
Density: 1.266 g/cm3
Flash Point: 39.5 °C
Enthalpy of Vaporization: 36.32 kJ/mol
Boiling Point: 141.7 °C at 760 mmHg
Vapour Pressure: 7.24 mmHg at 25°C
4-(Trifluoromethyl)pyridine (CAS NO.3796-24-5) is commonly used as pharmaceutical intermediate.
Hazard Codes of 4-(Trifluoromethyl)pyridine (CAS NO.3796-24-5): F,Xi
Risk Statements: 11-36/37/38
R11: Highly flammable.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 16-26-36-37/60
S16: Keep away from sources of ignition.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
S37: Wear suitable gloves.
S60: This material and its container must be disposed of as hazardous waste.
RIDADR: UN 1993 3/PG 2
WGK Germany: 3
Hazard Note: Irritant/Flammable
HazardClass: 3
PackingGroup: II
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