3-(trifluoromethyl)pyridine
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With 1% Pd on activated carbon; chlorine at 235℃; for 24h; Temperature; Reagent/catalyst; Inert atmosphere; | 94.9% |
2-chloro-5-(Trichloromethyl)-pyridine
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With hydrogen fluoride; mercury(II) oxide | 87% |
With antimony(III) fluoride for 0.166667h; Heating; | 54.5% |
With hydrogen fluoride | |
With hydrogen fluoride at 130℃; Temperature; |
3-Methylpyridine
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With magnesium fluoride; hydrogen fluoride; chlorine at 220 - 280℃; for 8h; Temperature; Reagent/catalyst; Inert atmosphere; | 76.7% |
2-chloro-5-trifluoromethylpyridine 1-oxide
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In dichloromethane at 31℃; for 16h; Sealed tube; Irradiation; | 59% |
3-(trifluoromethyl)pyridine-N-oxide
A
2-chloro-5-trifluoromethylpyridine
B
2-chloro-3-trifluoromethyl-pyridine
Conditions | Yield |
---|---|
Stage #1: 3-(trifluoromethyl)pyridine-N-oxide With trichlorophosphate In 1,2-dichloro-ethane at 105 - 125℃; for 7h; Stage #2: With triethylamine In 1,2-dichloro-ethane at -30 - -20℃; for 3h; | A 25.34% B 50.34% |
2-choro-5-iodopyridine
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With potassium fluoride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 90℃; for 4h; Sealed tube; Inert atmosphere; | 38% |
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; silver fluoride In N,N-dimethyl-formamide at 100℃; for 1h; Inert atmosphere; Sealed tube; chemoselective reaction; | 98 %Spectr. |
2-choro-5-iodopyridine
sodium 2,2,2-trifluoroacetate
A
2,5-bis(trifluoromethyl)pyridine
B
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; copper(l) iodide at 160℃; for 4h; | A 7 % Chromat. B 85 % Chromat. |
2-chloro-5-(Trichloromethyl)-pyridine
A
2-chloro-5-trifluoromethylpyridine
B
2-fluoro-5-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With antimony(III) fluoride |
6-Chloro-3-pyridinecarboxylic acid
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With hydrogen fluoride In (2S)-N-methyl-1-phenylpropan-2-amine hydrate | |
With hydrogen fluoride | |
With sodium hydroxide; hydrogen fluoride |
6-hydroxy-3-pyridinecarboxylic acid
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With phosphorus pentachloride In water |
2-hydroxy-5-(trifluoromethyl)pyridine
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With phosphorus pentachloride In water | |
With trichlorophosphate In N-methyl-acetamide; water |
antimony(III) fluoride
2-chloro-5-(Trichloromethyl)-pyridine
2-chloro-5-trifluoromethylpyridine
6-hydroxy-3-pyridinecarboxylic acid
5-(trifluoromethyl)-2(1H)-pyridone
phosphorus pentachloride
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With trichlorophosphate In water |
2-choro-5-iodopyridine
(trifluoromethyl)triethylsilane
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With potassium fluoride; copper(l) iodide; 1,10-Phenanthroline In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide at 20 - 60℃; Inert atmosphere; | 69 %Spectr. |
Langlois reagent
6-chloropyridin-3-ylboronic acid
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; tetrakis(actonitrile)copper(I) hexafluorophosphate; sodium hydrogencarbonate In methanol; water at 0 - 20℃; for 12h; | 85 %Spectr. |
2-cyclopropyl-1-(trifluoromethyl)benzo[b]thiophenium triflate
6-chloropyridin-3-ylboronic acid
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With 2,4,6-trimethyl-pyridine; fluorobenzene; copper diacetate In ethyl acetate at 20℃; for 20h; Inert atmosphere; | 16 %Spectr. |
(trifluoromethyl)trimethylsilane
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With potassium fluoride; copper(l) iodide; triphenylphosphine In N,N-dimethyl-formamide at 65℃; for 12h; regioselective reaction; | 72 %Spectr. |
3-Methylpyridine
A
2,6-dichloro-3-(trifluoromethyl)pyridine
B
2-chloro-5-trifluoromethylpyridine
C
2-chloro-3-trifluoromethyl-pyridine
Conditions | Yield |
---|---|
With hydrogen fluoride; chlorine at 200 - 400℃; for 30h; Large scale; | A 47.7 %Chromat. B 3.7 %Chromat. C 14.5 %Chromat. |
3-Hydroxybenzyl alcohol
2-chloro-5-trifluoromethylpyridine
[3-[[5-(trifluoromethyl)-2-pyridyl]oxy]phenyl]methanol
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 95 - 105℃; for 5h; Product distribution / selectivity; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 90 - 95℃; for 16h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 95℃; for 16h; Product distribution / selectivity; | 53% |
With potassium carbonate In N,N-dimethyl-formamide at 95℃; for 16h; | 53% |
With potassium carbonate In N,N-dimethyl-formamide at 95℃; for 16h; | 53% |
5-bromo-2-chlorophenol
2-chloro-5-trifluoromethylpyridine
2-(5-bromo-2-chlorophenoxy)-5-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20 - 110℃; for 12h; | 100% |
8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-3-{1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropyl}-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine
2-chloro-5-trifluoromethylpyridine
8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-3-(1-{4-[5-(trifluoromethyl)pyridin-2-yl]phenyl}cyclopropyl)-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 130℃; for 1.5h; Microwave irradiation; | 100% |
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 90℃; for 40h; Sealed tube; Inert atmosphere; | 100% |
3-Bromophenol
2-chloro-5-trifluoromethylpyridine
2-(3-bromophenoxy)-5-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 16h; Inert atmosphere; | 99% |
With potassium carbonate In N,N-dimethyl-formamide at 110℃; |
Thien-3-ylboronic acid
2-chloro-5-trifluoromethylpyridine
2-(thiophen-3-yl)-5-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With dichloro bis((p-dimethylaminophenyl)-ϖ-di-tert-butylphosphine)palladium(II); triethylamine In water at 20℃; for 19h; Suzuki-Miyaura coupling; Inert atmosphere; | 99% |
trimethoxonium tetrafluoroborate
2-chloro-5-trifluoromethylpyridine
C7H6ClF3N(1+)*BF4(1-)
Conditions | Yield |
---|---|
In dichloromethane at 20℃; | 99% |
triethyloxonium fluoroborate
2-chloro-5-trifluoromethylpyridine
1-ethyl-5-trifluoromethyl-2-chloropyridinium tetrafluoroborate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; | 99% |
2-chloro-5-trifluoromethylpyridine
4-tert-butylphenylboronic acid
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; nixantphos In tetrahydrofuran; water at 20℃; for 6h; Suzuki-Miyaura Coupling; | 99% |
2-chloro-5-trifluoromethylpyridine
tributyl(thien-2-yl)stannane
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In toluene for 16h; Inert atmosphere; Reflux; | 99% |
2,4-di-tert-Butylphenol
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With potassium tert-butylate In ammonia at -78℃; for 1h; Irradiation; add of 1,3-dinitrobenzene or galvinoxyl; | 98% |
2-chloro-5-trifluoromethylpyridine
Benzimidazol-2-thiol
Conditions | Yield |
---|---|
With potassium tert-butylate for 0.5h; Irradiation; | 98% |
With sodium hydroxide 2.) DMF, reflux, 3 h; Yield given. Multistep reaction; |
2-chloro-5-trifluoromethylpyridine
2-hydroxyethanethiol
Conditions | Yield |
---|---|
With potassium tert-butylate for 0.166667h; Irradiation; | 98% |
2-chloro-5-trifluoromethylpyridine
di-4-methoxyphenylzinc
2-(4-methoxyphenyl)-5-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With tripiperidino-phosphine; nickel dichloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 60℃; for 1h; Negishi cross-coupling reaction; | 98% |
2-chloro-5-trifluoromethylpyridine
1H-Pyrazolo[3,4-b]pyridine
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; zinc diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 16h; Buchwald-Hartwig Coupling; Inert atmosphere; | 98% |
2-chloro-5-trifluoromethylpyridine
hydroquinone
2-(4-hydroxyphenoxy)-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With sodium hydrogensulfite; potassium hydroxide In N,N-dimethyl-formamide at 50 - 90℃; for 6h; Temperature; Reagent/catalyst; | 97.8% |
With potassium carbonate In N,N-dimethyl-formamide at 60 - 90℃; for 4h; | 75% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; |
N,N-dimethyl-cyclohexanamine
2-chloro-5-trifluoromethylpyridine
A
N,N-dimethyl-5-(trifluoromethyl)pyridine-2-amine
B
Cyclohexyl-methyl-(5-trifluoromethyl-pyridin-2-yl)-amine
Conditions | Yield |
---|---|
In tetrahydrofuran at 100℃; under 6000480 Torr; for 96h; | A 2% B 97% |
2-chloro-5-trifluoromethylpyridine
5,5’-bis(trifluoromethyl)-2,2’-bipyridine
Conditions | Yield |
---|---|
With potassium hydroxide In water; N,N-dimethyl-formamide at 35℃; for 12h; Ullmann Condensation; Inert atmosphere; | 97% |
With manganese; nickel(II) bromide trihydrate In N,N-dimethyl-formamide at 20 - 60℃; for 20h; Inert atmosphere; | 70% |
With [2,2]bipyridinyl; nickel diacetate; sodium tert-pentoxide In tetrahydrofuran at 25℃; for 0.0377778h; | 57% |
2-chloro-5-trifluoromethylpyridine
2-mercapto-3H-quinazolin-4-one
Conditions | Yield |
---|---|
With potassium tert-butylate for 0.416667h; Irradiation; | 97% |
2-chloro-5-trifluoromethylpyridine
ethyl 3-methylpyrazole-4-carboxylate
Conditions | Yield |
---|---|
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 100℃; | 97% |
2-chloro-5-trifluoromethylpyridine
2,4-dimethoxypyrimidin-5-ylboronic acid
2,4-dimethoxy-5-(5-(trifluoromethyl)pyridin-2-yl)pyrimidine
Conditions | Yield |
---|---|
With potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); tetrabutylammomium bromide In 1-methyl-pyrrolidin-2-one; water; toluene at 90℃; for 5h; Suzuki-Miyaura cross-coupling; Continuous flow reactor; Inert atmosphere; | 97% |
2-chloro-5-trifluoromethylpyridine
4-hydroxy-benzaldehyde
4-((5-(trifluoromethyl)pyridin-2-yl)oxy)benzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 140℃; for 10h; | 97% |
Stage #1: 4-hydroxy-benzaldehyde With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 2-chloro-5-trifluoromethylpyridine In N,N-dimethyl-formamide at 20 - 105℃; for 10h; |
dmap
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 120℃; for 3h; Temperature; | 97% |
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide In n-heptane; water | 96.3% |
In ice-water; N,N-dimethyl-formamide | 67% |
N,N'-dimethylbenzylamine
2-chloro-5-trifluoromethylpyridine
A
N,N-dimethyl-5-(trifluoromethyl)pyridine-2-amine
Conditions | Yield |
---|---|
In tetrahydrofuran at 100℃; under 6000480 Torr; for 96h; | A 96% B 2% |
2-chloro-5-trifluoromethylpyridine
4-methoxy-phenol
5-(trifluoromethyl)-2-(4-methoxyphenoxy)pyridine
Conditions | Yield |
---|---|
With aluminum oxide; potassium fluoride In N,N-dimethyl-formamide at 120℃; for 5h; | 96% |
In water; dimethyl sulfoxide |
2-chloro-5-trifluoromethylpyridine
phenylboronic acid
2-phenyl-5-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; nixantphos In tetrahydrofuran; water at 20℃; for 6h; Suzuki-Miyaura Coupling; | 96% |
Stage #1: 2-chloro-5-trifluoromethylpyridine; phenylboronic acid With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl In dodecane; butan-1-ol at 25℃; for 0.0833333h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox; Stage #2: With cesiumhydroxide monohydrate In dodecane; water; butan-1-ol at 25℃; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox; | 95% |
With dichloro bis((p-dimethylaminophenyl)-ϖ-di-tert-butylphosphine)palladium(II); triethylamine In water at 20℃; for 24h; Suzuki-Miyaura coupling; Inert atmosphere; | 94% |
p-hydroxymethylphenylboronic acid
2-chloro-5-trifluoromethylpyridine
[4-(5-trifluoromethyl-pyridin-2-yl)-phenyl]-methanol
Conditions | Yield |
---|---|
With C37H44ClN2O3PPd; caesium carbonate In water at 100℃; for 12h; Suzuki Coupling; Schlenk technique; Inert atmosphere; | 96% |
palladium dichloride |
ethyl 3-isopropyl-1H-pyrazole-4-carboxylate
2-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 100℃; | 96% |
2-chloro-5-trifluoromethylpyridine
(RS)-2-methylpiperazine
3-methyl-1-(5-trifluoromethyl-pyridin-2-yl)-piperazine
Conditions | Yield |
---|---|
With triethylamine In toluene at 150℃; for 20h; | 96% |
The IUPAC name of 2-Chloro-5-(trifluoromethyl)pyridine is 2-chloro-5-(trifluoromethyl)pyridine. With the CAS registry number 52334-81-3, it is also named as Pyridine, 2-chloro-5-(trifluoromethyl)-. The product's categories are Blocks; Fluoro Compounds; Pyridines; Pyridine; Pyridines, Pyrimidines, Purines and Pteredines; Pyridine Series; Halides; Pyridines Derivates; Chloropyridines; Halopyridines; C6 Heterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks. Besides, it is white to yellowish crystalline low melting solid, which should be stored in tightly sealed containers in a cool, dry place at 0-6 °C. And you should ensure that the workplaces have good ventilated or exhaust devices. In addition, its molecular formula is C6H3ClF3N and molecular weight is 181.54.
The other characteristics of this product can be summarized as: (1)EINECS: 257-856-5; (2)ACD/LogP: 2.32; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 2.315; (5)ACD/LogD (pH 7.4): 2.315; (6)ACD/BCF (pH 5.5): 33.837; (7)ACD/BCF (pH 7.4): 33.837; (8)ACD/KOC (pH 5.5): 432.864; (9)ACD/KOC (pH 7.4): 432.864; (10)#H bond acceptors: 1; (11)#H bond donors: 0; (12)#Freely Rotating Bonds: 0; (13)Polar Surface Area: 12.89 Å2; (14)Index of Refraction: 1.447; (15)Molar Refractivity: 34.219 cm3; (16)Molar Volume: 128.118 cm3; (17)Polarizability: 13.565×10-24cm3; (18)Surface Tension: 27.918 dyne/cm; (19)Density: 1.417 g/cm3; (20)Flash Point: 57.604 °C; (21)Melting Point: 29-33 °C; (22)Enthalpy of Vaporization: 39.126 kJ/mol; (23)Boiling Point: 171.636 °C at 760 mmHg; (24)Vapour Pressure: 1.844 mmHg at 25 °C.
Preparation of 2-Chloro-5-(trifluoromethyl)pyridine: frist of all, you can use Cl2 to react with 2-Chloro-5-methylpyridine. And you would obtain 2-Chloro-5-trichloromethylpyridine. Then you will get this chemical by fluorination.
Uses of 2-Chloro-5-(trifluoromethyl)pyridine: this chemical can be used as an intermediate of Fluazifop. What's more, it can react with [1,4]diazepane to get 1,4-bis-(5-trifluoromethyl-pyridin-2-yl)-[1,4]diazepane.
This reaction needs triethylamine, polytetrafluoroethylene (PTFE) and tetrahydrofuran at temperature of 100 °C for 4 days. The yield is 89 %.
When you are using this chemical, please be cautious about it as the following: it is highly flammable, so please keep away from sources of ignition. It is also harmful by inhalation, in contact with skin and if swallowed. And it is toxic if swallowed. Please do not breathe dust. Moreover, it irritates to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection. Additionally, in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
People can use the following data to convert to the molecule structure.
(1)Canonical SMILES: C1=CC(=NC=C1C(F)(F)F)Cl
(2)InChI: InChI=1S/C6H3ClF3N/c7-5-2-1-4(3-11-5)6(8,9)10/h1-3H
(3)InChIKey: JFZJMSDDOOAOIV-UHFFFAOYSA-N
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