2,3-dichloro-5-(trichloromethyl)pyridine
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With hydrogen fluoride; tungsten(VI) chloride at 170 - 180℃; under 1500.15 Torr; for 5h; Reagent/catalyst; Temperature; Pressure; Autoclave; | 92% |
With antimony(III) fluoride for 0.166667h; Heating; Irradiation; | 80.4% |
With pyridine; iron(III) chloride; hydrogen fluoride at 130 - 175℃; Autoclave; | 73% |
2,2-dichloro-3,3,3-trifluoro-propionaldehyde
acrylonitrile
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
copper(l) chloride In acetonitrile at 190℃; for 0.5h; | 60% |
antimony(III) fluoride
2,3-dichloro-5-(trichloromethyl)pyridine
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With antimonypentachloride |
2-chloro-5-trifluoromethylpyridine
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With iron(III) chloride In water | |
With antimonypentachloride; iron(III) chloride In water | |
With chlorine; iron(III) chloride | |
Stage #1: 2-chloro-5-trifluoromethylpyridine under 15001.5 Torr; for 2h; Autoclave; Inert atmosphere; Stage #2: With chlorine at 0 - 150℃; under 15001.5 Torr; for 20h; Temperature; Reagent/catalyst; Inert atmosphere; |
2-chloro-5-trifluoromethylpyridine
tungsten(VI) chloride
2,3-dichloro-5-trifluoromethylpyridine
2-fluoro-3-chloro-5-(trifluoromethyl)pyridine
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With FeCl3 |
nickel
2-fluoro-3-chloro-5-(trifluoromethyl)pyridine
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With FeCl3 In (2S)-N-methyl-1-phenylpropan-2-amine hydrate |
2,3-dichloro-5-trifluoromethylpyridine
3-trichloromethyl-pyridine
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: phosphorus pentachloride / 16 h / 210 °C / Autoclave 2: hydrogen fluoride; iron(III) chloride; pyridine / 130 - 175 °C / Autoclave View Scheme | |
Multi-step reaction with 3 steps 1: phosphorus pentachloride / 16 h / 210 °C / Autoclave 2: phosphorus pentachloride / 16 h / 210 °C / Autoclave 3: hydrogen fluoride; iron(III) chloride; pyridine / 130 - 175 °C / Autoclave View Scheme |
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: phosphorus pentachloride / 16 h / 210 °C / Autoclave 2: hydrogen fluoride; iron(III) chloride; pyridine / 130 - 175 °C / Autoclave View Scheme |
nicotinic acid
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: phosphorus pentachloride / 14 h / 210 °C / 1500.15 - 27752.8 Torr / Autoclave 2: hydrogen fluoride; iron(III) chloride; pyridine / 130 - 175 °C / Autoclave View Scheme | |
Multi-step reaction with 2 steps 1: phosphorus pentachloride / 64 h / 185 °C / 18751.9 - 30003 Torr / Autoclave 2: hydrogen fluoride; iron(III) chloride; pyridine / 130 - 175 °C / Autoclave View Scheme | |
Multi-step reaction with 2 steps 1: phosphorus pentachloride / 72 h / 185 °C / 18751.9 - 30003 Torr / Autoclave 2: hydrogen fluoride; iron(III) chloride; pyridine / 130 - 175 °C / Autoclave View Scheme |
3-Methylpyridine
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: tetrachloromethane; chlorine / 0 h / 350 - 400 °C 2: chlorine / 6 h / 150 - 160 °C 3: hydrogen fluoride / 11 h / 170 °C View Scheme |
2-chloro-5-(Trichloromethyl)-pyridine
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: chlorine / 6 h / 150 - 160 °C 2: hydrogen fluoride / 11 h / 170 °C View Scheme |
2-chloro-5-trifluoromethylpyridine
A
2,6-dichloro-3-(trifluoromethyl)pyridine
B
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
Stage #1: 2-chloro-5-trifluoromethylpyridine under 15001.5 Torr; for 2h; Autoclave; Inert atmosphere; Stage #2: With chlorine at 0 - 150℃; under 15001.5 Torr; for 20h; Reagent/catalyst; Inert atmosphere; |
2-chloro-5-trifluoromethylpyridine
A
2,3,6-trichloro-5-trifluoromethylpyridine
B
2,6-dichloro-3-(trifluoromethyl)pyridine
C
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
Stage #1: 2-chloro-5-trifluoromethylpyridine under 15001.5 Torr; for 2h; Autoclave; Inert atmosphere; Stage #2: With chlorine at 0 - 200℃; under 15001.5 Torr; for 20h; Inert atmosphere; |
2,3-dichloro-5-trifluoromethylpyridine
2-fluoro-3-chloro-5-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With potassium carbonate; cesium fluoride In dimethyl sulfoxide at 120℃; under 18.7519 - 22.5023 Torr; for 4h; Product distribution / selectivity; | 100% |
With potassium carbonate; cesium fluoride In 1-methyl-pyrrolidin-2-one at 70℃; for 1 - 3h; Product distribution / selectivity; | 98% |
With potassium fluoride; N-benzyl-N,N,N-triethylammonium chloride In N,N-dimethyl acetamide at 170℃; for 5h; Temperature; | 97% |
2,6-dimethyl-4-nitro phenol
2,3-dichloro-5-trifluoromethylpyridine
3-chloro-2-(2,6-dimethyl-4-nitrophenoxy)-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With potassium carbonate In ISOPROPYLAMIDE; water; ethyl acetate | 100% |
With potassium carbonate In ISOPROPYLAMIDE at 155 - 165℃; for 1h; | 100% |
salicylaldehyde
2,3-dichloro-5-trifluoromethylpyridine
2-([3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy)benzaldehyde
Conditions | Yield |
---|---|
Stage #1: salicylaldehyde With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: 2,3-dichloro-5-trifluoromethylpyridine In N,N-dimethyl-formamide; mineral oil at 0 - 50℃; for 2h; | 100% |
2,3-dichloro-5-trifluoromethylpyridine
tert-butyl methyl(piperidin-4-yl)carbamate
Conditions | Yield |
---|---|
With potassium carbonate at 100 - 120℃; | 100% |
With potassium tert-butylate; palladium diacetate; DavePhos In toluene at 120℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere; | 63% |
3-(tert-butoxycarbonylamino)pyrrolidine
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With potassium carbonate at 100 - 120℃; | 100% |
5-tert-butoxycarbonylamino-1-aminopentane
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With potassium carbonate at 100 - 120℃; | 100% |
(endo)-(8-aza-bicyclo[3.2.1]oct-3-yl)-carbamic acid tert-butyl ester
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With potassium carbonate at 100 - 120℃; | 100% |
2,3-dichloro-5-trifluoromethylpyridine
acetonitrile
2‐[3‐chloro‐5‐(trifluoromethyl)pyridin‐2‐yl]acetonitrile
Conditions | Yield |
---|---|
With sodium methylate at 130℃; under 21002.1 Torr; for 16h; Pressure; Temperature; Reagent/catalyst; Inert atmosphere; | 99.2% |
copper
2,3-dichloro-5-trifluoromethylpyridine
thiophenol
3-chloro-2-phenylthio-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
99% |
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With potassium carbonate at 100 - 120℃; | 99% |
2,3-dichloro-5-trifluoromethylpyridine
t-butyl piperidin-3-ylcarbamate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; | 99% |
nitromethane
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride; potassium hydroxide at 15℃; Concentration; Temperature; Reagent/catalyst; | 98.7% |
With potassium tert-butylate In dimethyl sulfoxide at 0 - 27℃; for 14.25h; | 95.7% |
With potassium hydroxide In dimethyl sulfoxide at 20 - 50℃; for 3.25h; | 73.9% |
With potassium hydroxide In dimethyl sulfoxide at 20℃; |
2,3-dichloro-5-trifluoromethylpyridine
3-chloro-5-(trifluoromethyl)-pyridin-2-yl-hydrazine
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol at 50℃; for 2h; | 98.3% |
With hydrazine hydrate In ethanol Reflux; | 86% |
With hydrazine hydrate In ethanol at 40℃; for 24h; | 85.8% |
5-amino-2-chlorophenol
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With potassium carbonate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In toluene at 60℃; for 1h; Reagent/catalyst; Temperature; | 98.2% |
2,6-dichloro-4-benzyloxyphenol
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | 98% |
tert-Butyl acrylate
2,3-dichloro-5-trifluoromethylpyridine
tert-butyl 3-(3-chloro-2-oxo-5-(trifluoromethyl)pyridin-1(2H)-yl)propanoate
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; oxygen; silver(I) acetate; palladium diacetate; Trimethylacetic acid In N,N-dimethyl-formamide at 130℃; under 760.051 Torr; for 20h; | 98% |
2,3-dichloro-5-trifluoromethylpyridine
acrylonitrile
3-(3-chloro-2-oxo-5-(trifluoromethyl)pyridin-1(2H)-yl)propanenitrile
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; oxygen; silver(I) acetate; palladium diacetate; Trimethylacetic acid In N,N-dimethyl-formamide at 130℃; under 760.051 Torr; for 20h; | 98% |
1-amino-4-[(tert-butyloxycarbonyl)amino]butane
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With potassium carbonate at 100 - 120℃; | 98% |
N-(p-tolyl)-1H-pyrrole-2-carboxamide
2,3-dichloro-5-trifluoromethylpyridine
5-(p-tolyl)-3-(trifluoromethyl)pyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile for 7h; Reflux; | 97% |
2,3-dichloro-5-trifluoromethylpyridine
ethyl 2-cyanoacetate
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 50℃; for 1h; | 97% |
Stage #1: 2,3-dichloro-5-trifluoromethylpyridine With potassium carbonate In dimethyl sulfoxide at 20℃; for 0.25h; Stage #2: ethyl 2-cyanoacetate In dimethyl sulfoxide at 80℃; for 2.5h; | 90.6% |
With potassium hydroxide In 1-methyl-pyrrolidin-2-one at 70 - 80℃; for 2.5h; | |
Stage #1: ethyl 2-cyanoacetate With tetrabutyl-ammonium chloride; sodium methylate In methanol at 25℃; for 0.5h; Stage #2: 2,3-dichloro-5-trifluoromethylpyridine In methanol at 70℃; for 1h; Reagent/catalyst; Solvent; | |
Stage #1: 2,3-dichloro-5-trifluoromethylpyridine; ethyl 2-cyanoacetate With potassium carbonate In dimethyl sulfoxide at 70℃; for 12h; Stage #2: With hydrogenchloride In water |
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; | 97% |
(R)-piperidin-3-ylcarbamic acid tert-butyl ester
2,3-dichloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 5h; | 97% |
2,3-dichloro-5-trifluoromethylpyridine
2-(4'-hydroxyphenoxy)-3-chloro-5-trifluoromethylpyridine
Conditions | Yield |
---|---|
96.9% | |
96.9% | |
93.5% |
3-isopropyl-4-[3-(methoxymethoxy)propyl]-1H-pyrazole
2,3-dichloro-5-trifluoromethylpyridine
1-[3-chloro-5-(trifluoromethyl)-2-pyridyl]-3-isopropyl-4-[3-(methoxymethoxy)propyl]-1H-pyrazole
Conditions | Yield |
---|---|
With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 50℃; | 96% |
acrylic acid n-butyl ester
2,3-dichloro-5-trifluoromethylpyridine
butyl 3-(3-chloro-2-oxo-5-(trifluoromethyl)pyridin-1(2H)-yl)propanoate
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; oxygen; silver(I) acetate; palladium diacetate; Trimethylacetic acid In N,N-dimethyl-formamide at 130℃; under 760.051 Torr; for 20h; Catalytic behavior; Reagent/catalyst; | 96% |
2,3-dichloro-5-trifluoromethylpyridine
acrylic acid methyl ester
methyl 3-(3-chloro-2-oxo-5-(trifluoromethyl)pyridin-1(2H)-yl)propanoate
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; oxygen; silver(I) acetate; palladium diacetate; Trimethylacetic acid In N,N-dimethyl-formamide at 130℃; under 760.051 Torr; for 20h; | 96% |
2,3-dichloro-5-trifluoromethylpyridine
phenylboronic acid
3-chloro-2-phenyl-5-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; triphenylphosphine In methanol; acetonitrile at 50℃; for 24h; Suzuki Coupling; Inert atmosphere; regioselective reaction; | 96% |
ethanol
carbon monoxide
2,3-dichloro-5-trifluoromethylpyridine
diethyl 5-(trifluoromethyl)pyridine-2,3-dicarboxylate
Conditions | Yield |
---|---|
With sodium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride at 120℃; under 11251.1 Torr; for 18h; | 95% |
With 1,1'-bis-(diphenylphosphino)ferrocene; sodium acetate; palladium diacetate at 150℃; under 11400.8 Torr; for 2h; Autoclave; | 92% |
With 1,1'-bis(diphenylphosphino)ferrocene; palladium diacetate |
2,3-dichloro-5-trifluoromethylpyridine
(R)-2-(4-hydroxyphenoxy)propionic acid
(R)-2-[4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)phenoxy]propanoic acid
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | 95% |
Stage #1: (R)-2-(4-hydroxyphenoxy)propionic acid With potassium carbonate In N,N-dimethyl-formamide at 70 - 80℃; for 1h; Stage #2: 2,3-dichloro-5-trifluoromethylpyridine at 70 - 80℃; for 8h; | 84.4% |
Stage #1: (R)-2-(4-hydroxyphenoxy)propionic acid With potassium carbonate In N,N-dimethyl-formamide at 70 - 80℃; for 1h; Stage #2: 2,3-dichloro-5-trifluoromethylpyridine In N,N-dimethyl-formamide at 70 - 80℃; for 8h; | 84.4% |
IUPAC Name: 2,3-Dichloro-5-(trifluoromethyl)pyridine
Canonical SMILES: C1=C(C=NC(=C1Cl)Cl)C(F)(F)F
InChI: InChI=1S/C6H2Cl2F3N/c7-4-1-3(6(9,10)11)2-12-5(4)8/h1-2H
InChIKey: ABNQGNFVSFKJGI-UHFFFAOYSA-N
Empirical Formula: C6H2Cl2F3N
Molecular Weight: 215.988
EINECS: 410-340-5
Product Categories: Halides; Pyridines; Pyridine; Pyridine series; Chloropyridines; Halopyridines; C6Heterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks
Appearance: Light yellow liquid
Index of Refraction: 1.47
Molar Refractivity: 39.11 cm3
Molar Volume: 140 cm3
Surface Tension: 30.9 dyne/cm
Density: 1.542 g/cm3
Flash Point: 79.4 °C
Enthalpy of Vaporization: 40.73 kJ/mol
Boiling Point: 188.5 °C at 760 mmHg
Vapour Pressure: 0.825 mmHg at 25°C
Melting Point of 2,3-Dichloro-5-trifluoromethyl pyridine (CAS NO.69045-84-7): 8-9 °C
Hazard Codes: Xn,Xi, N
Risk Statements:
41: Risk of serious damage to eyes
43: May cause sensitization by skin contact
20/22: Harmful by inhalation and if swallowed
36/37/38: Irritating to eyes, respiratory system and skin
51/53: Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
Safety Statements:
24: Avoid contact with skin
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
61: Avoid release to the environment. Refer to special instructions safety data sheet
37/39: Wear suitable gloves and eye/face protection
RIDADR:UN 3082 9/PG 3
WGK Germany:2
Hazard Note:Irritant
2,3-Dichloro-5-trifluoromethyl pyridine (CAS NO.69045-84-7), its Synonyms are Pyridine, 2,3-dichloro-5-(trifluoromethyl)- ; 2,3-Dichloro-5-(trifluoromethyl)pyridine .
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