3-Chloro-5-trifluoromethylpyridine-2-carbonitrile supplier

Name
2-Cyano-3-chloro-5-(trifluoromethyl)-pyridine
EINECS
CAS No. 80194-70-3
Article Data16
CAS DataBase
Density 1.51 g/cm³
Solubility
Melting Point
Formula C₇H₂ClF₃N₂
Boiling Point 250.4 °C at 760 mmHg
Molecular Weight 206.554
Flash Point 105.2 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-Pyridinecarbonitrile, 3-chloro-5-(trifluoromethyl)-;
PSA 36.68000
LogP 2.62548

Synthetic route

: potassium cyanide

: 69045-84-7
2,3-dichloro-5-trifluoromethylpyridine

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
Stage #1: 2,3-dichloro-5-trifluoromethylpyridine With dmap In acetone for 5h; Reflux; Large scale; Stage #2: potassium cyanide In dichloromethane; water at 10℃; for 2h; Large scale;	91%
dmap In acetonitrile at 84℃; for 10h; Conversion of starting material;

: 72537-17-8
2-fluoro-3-chloro-5-(trifluoromethyl)pyridine

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
With potassium cyanide; Aliquat 336 In water at 30℃; for 5h;	90%
With sodium cyanide; tetrabutylammomium bromide at 20 - 25℃; for 23h;	82%

: 773837-37-9
sodium cyanide

: 72537-17-8
2-fluoro-3-chloro-5-(trifluoromethyl)pyridine

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
Stage #1: 2-fluoro-3-chloro-5-(trifluoromethyl)pyridine With dmap In acetone for 5h; Reflux; Large scale; Stage #2: sodium cyanide In chloroform; water at 20℃; for 2.5h; Large scale;	89%
dmap In water; propiononitrile at 20℃; for 5h;	83%
With tetrabutylammomium bromide In water; dimethyl sulfoxide at 45 - 50℃; Concentration;	74.3%
With N-benzyl-N,N,N-triethylammonium chloride at 20℃; for 10h; Temperature;	46.7 g

: 75806-84-7
2-bromo-3-chloro-5-(trifluoromethyl)pyridine

: 788104-34-7, 25733-05-5
lithium cyanide

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
Stage #1: 2-bromo-3-chloro-5-(trifluoromethyl)pyridine With 4-pyrrolidin-1-ylpyridine In ethanol for 6h; Reflux; Large scale; Stage #2: lithium cyanide In water; 1,2-dichloro-ethane at 80℃; for 2h; Large scale;	88.1%

: potassium cyanide

: 107-06-2
1,2-dichloro-ethane

: 72537-17-8
2-fluoro-3-chloro-5-(trifluoromethyl)pyridine

A: 110-61-2
butanedinitrile

B: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
With dmap In water at 75 - 78℃; for 12h; Reagent/catalyst; Temperature;	A 81.8% B 86.7%

...Expand

: 74-90-8
hydrogen cyanide

: 69045-84-7
2,3-dichloro-5-trifluoromethylpyridine

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
Stage #1: 2,3-dichloro-5-trifluoromethylpyridine With triethylamine In methanol for 4h; Reflux; Large scale; Stage #2: hydrogen cyanide In dichloromethane; water at 0℃; for 3h; Large scale;	85.7%

: 151-50-8
potassium cyanide

: 72537-17-8
2-fluoro-3-chloro-5-(trifluoromethyl)pyridine

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
In dimethyl sulfoxide at 30℃; for 0.833333h;	84%

: 143-33-9
sodium cyanide

: 69045-84-7
2,3-dichloro-5-trifluoromethylpyridine

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
Stage #1: 2,3-dichloro-5-trifluoromethylpyridine With dmap In propiononitrile Heating / reflux; Stage #2: sodium cyanide In water; propiononitrile for 5h;	75.7%

: 773837-37-9
sodium cyanide

: 69045-84-7
2,3-dichloro-5-trifluoromethylpyridine

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
Stage #1: 2,3-dichloro-5-trifluoromethylpyridine; dmap In propiononitrile for 5h; Heating / reflux; Stage #2: sodium cyanide In water at 15℃; for 5h;	73%
dmap In 1,2-dimethoxyethane at 85℃; for 4h; Conversion of starting material;
dmap In acetonitrile at 82℃; for 21h; Conversion of starting material;
dmap In propiononitrile at 98℃; for 10.5h; Conversion of starting material;
In N,N-dimethyl-formamide at 120℃; for 8h;

: 10442-39-4
tetra-n-butylammonium cyanide

: 69045-84-7
2,3-dichloro-5-trifluoromethylpyridine

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
dmap In propiononitrile at 98℃; for 4h; Conversion of starting material;

: 75806-84-7
2-bromo-3-chloro-5-(trifluoromethyl)pyridine

: copper(l) cyanide

: ammonium hydroxide

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
In N-methyl-acetamide; diethyl ether

...Expand

: 246022-23-1
3-chloro-5-(trifluoromethyl)picolinaldehydeoxime

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
With Burgess Reagent In tetrahydrofuran at 65℃; for 1h;
With Burgess Reagent In tetrahydrofuran at 65℃; for 1h;

: 175277-74-4
(3-chloro-5-trifluoromethyl-pyridin-2-yl)methylamine

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
With ammonium hydroxide; oxygen In tert-Amyl alcohol at 110℃; under 2250.23 Torr; for 15h; Autoclave; Green chemistry;	92 %Chromat.

: 175277-50-6
3-chloro-5-(trifluoromethyl)picolinaldehyde

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; pyridine / ethanol / 1 h / 95 °C 2: Burgess Reagent / tetrahydrofuran / 1 h / 65 °C View Scheme
Multi-step reaction with 2 steps 1: pyridine; hydroxylamine hydrochloride / ethanol / 1 h / 95 °C 2: Burgess Reagent / tetrahydrofuran / 1 h / 65 °C View Scheme

: 69045-84-7
2,3-dichloro-5-trifluoromethylpyridine

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium fluoride / dimethyl sulfoxide / 115 - 120 °C / Inert atmosphere 2: tetrabutylammomium bromide / dimethyl sulfoxide; water / 45 - 50 °C View Scheme

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

: 80194-71-4
3-fluoro-5-(trifluoromethyl)picolinonitrile

Conditions

Conditions	Yield
With potassium carbonate; cesium fluoride In dimethyl sulfoxide at 80 - 95℃; for 0.5h;	100%
With N-benzyl-N,N,N-triethylammonium chloride; sodium fluoride In N,N-dimethyl acetamide at 125 - 130℃; under 760.051 Torr; for 15h; Reagent/catalyst; Large scale;	95.2%
With potassium carbonate; dimethyl sulfoxide; cesium fluoride
With potassium carbonate; dimethyl sulfoxide; cesium fluoride
With potassium carbonate; dimethyl sulfoxide; cesium fluoride

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

: 175277-74-4
(3-chloro-5-trifluoromethyl-pyridin-2-yl)methylamine

Conditions

Conditions	Yield
Stage #1: 3-chloro-2-cyano-5-(trifluoromethyl)pyridine With sodium hydroxide In methanol at 70℃; Stage #2: With sodium hypochlorite In methanol at 10℃; Solvent; Reagent/catalyst; Temperature;	98%
With sulfuric acid; 20% palladium hydroxide-activated charcoal; tetrabutylammomium bromide; hydrogen In methanol at 20℃; under 15001.5 Torr;	96.4%

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

: 64-19-7
acetic acid

: 1-[-3-chloro-5-(trifluoromethyl)pyridin-2-yl]methanamine acetate

Conditions

Conditions	Yield
With hydrogen at 80℃; under 750.075 - 1500.15 Torr; for 15h; Temperature; Pressure; Autoclave;	97.8%

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

A: 175277-74-4
(3-chloro-5-trifluoromethyl-pyridin-2-yl)methylamine

B: 164341-39-3
1-[5-(trifluoromethyl)pyridin-2-yl]methanamine

Conditions

Conditions	Yield
With hydrogen; acetic acid; nickel at 40 - 45℃; under 13501.4 Torr; for 4h;	A 97% B 0.05%

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

: 871826-12-9
1-[5-(trifluoromethyl)-2-pyridinyl]methanamine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; 5% rhodium-on-charcoal; hydrogen In methanol; water at 100℃; under 7500.75 - 11251.1 Torr; for 10h; Catalytic behavior; Pressure; Autoclave;	96.5%

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

: 64-19-7
acetic acid

: 2-aminomethyl-5-trifluoromethylpyridine acetic acid

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethanol; water at 80℃; under 30003 - 33753.4 Torr; for 3h; Catalytic behavior; Pressure; Temperature; Autoclave;	96.4%

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

: [3-chloro-5-(trifluoromethyl)-pyridin-2-yl]methanamine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol; water at 20℃; under 760.051 Torr; for 4h;	95%

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

: 2-aminomethyl-5-trifluoromethylpyridine sulfate

Conditions

Conditions	Yield
With sulfuric acid; 5% active carbon-supported ruthenium; hydrogen In water; isopropyl alcohol at 30℃; under 30003 - 33753.4 Torr; for 10h; Autoclave;	95%

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

: 105-56-6
ethyl 2-cyanoacetate

: ethyl 2-cyano-2-[2-cyano-5-(trifluoromethyl)-3-pyridyl]acetate

Conditions

Conditions	Yield
Stage #1: ethyl 2-cyanoacetate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: 3-chloro-2-cyano-5-(trifluoromethyl)pyridine In N,N-dimethyl-formamide at 70℃; for 2h;	91%

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

: 64-17-5
ethanol

: 3-chloro-5-trifluoromethylpyridine-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
Stage #1: 3-chloro-2-cyano-5-(trifluoromethyl)pyridine; ethanol With pyridine; hydrogenchloride at 0 - 80℃; for 19h; Pinner Imino Ether Synthesis; Stage #2: In water at 25 - 30℃; for 2h; Concentration; Temperature;	87.6%

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

: 367-27-1
2,4-difluorophenol

: 3-(2,4-difluorophenoxy)-5-trifluoromethylpyridine-2-carbonitrile

Conditions

Conditions	Yield
Stage #1: 2,4-difluorophenol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 3-chloro-2-cyano-5-(trifluoromethyl)pyridine In N,N-dimethyl-formamide for 1h; Inert atmosphere;	71%

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

: 139-02-6
sodium phenoxide

: 1065607-70-6
3-phenoxy-5-(trifluoromethyl)picolinonitrile

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 1h;	67.5%

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

: 75-16-1
methylmagnesium bromide

: 207994-12-5
1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanone

Conditions

Conditions	Yield
Stage #1: 3-chloro-2-cyano-5-(trifluoromethyl)pyridine; methylmagnesium bromide In tetrahydrofuran; toluene at -5 - 20℃; for 7h; Stage #2: With hydrogenchloride; water In tetrahydrofuran; toluene at 20℃; for 3h;	46%
Stage #1: 3-chloro-2-cyano-5-(trifluoromethyl)pyridine; methylmagnesium bromide In tetrahydrofuran; toluene at 0 - 20℃; for 7h; Stage #2: With hydrogenchloride In tetrahydrofuran; water; toluene at 20℃; for 3h;	40%

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

: 164341-39-3
1-[5-(trifluoromethyl)pyridin-2-yl]methanamine

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethanol; water at 60℃; under 15001.5 - 18751.9 Torr; for 25h; Autoclave;	38%

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

: 80194-68-9
3-chloro-5-trifluoromethylpyridine-2-carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide In diethyl ether; ethanol; water

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

: 115377-94-1
2-(tert-butoxycarbonylamino)phenylboronic acid

: 1186635-27-7
2-(trifluoromethyl)benzo[f][1,7]naphthyridin-5-amine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 100℃; Suzuki Coupling;
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 100℃;

: 80194-70-3
3-chloro-2-cyano-5-(trifluoromethyl)pyridine

: 367-27-1
2,4-difluorophenol

: 3-(2,4-difluorophenoxy)-5-trifluoromethylpyridine-2-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere 1.2: 1 h / Inert atmosphere 2.1: sulfuric acid / 2 h / 50 °C / Inert atmosphere View Scheme

3-Chloro-5-trifluoromethylpyridine-2-carbonitrile Specification

The 3-Chloro-2-cyano-5-(trifluoromethyl)pyridine, with the CAS registry number 80194-70-3, is also known as 2-Pyridinecarbonitrile, 3-chloro-5-(trifluoromethyl)-. This chemical's molecular formula is C₇H₂ClF₃N₂ and molecular weight is 206.5524. What's more, its systematic name is 3-Chloro-5-(trifluoromethyl)pyridine-2-carbonitrile.

Physical properties about 3-Chloro-2-cyano-5-(trifluoromethyl)pyridine are: (1)ACD/LogP: 2.89; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.89; (4)ACD/LogD (pH 7.4): 2.89; (5)ACD/BCF (pH 5.5): 92.08; (6)ACD/BCF (pH 7.4): 92.08; (7)ACD/KOC (pH 5.5): 886.28; (8)ACD/KOC (pH 7.4): 886.28; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 36.68 Å²; (13)Index of Refraction: 1.482; (14)Molar Refractivity: 38.93 cm³; (15)Molar Volume: 136.4 cm³; (16)Polarizability: 15.43×10^-24 cm³; (17)Surface Tension: 42.1 dyne/cm; (18)Density: 1.51 g/cm³; (19)Flash Point: 105.2 °C; (20)Enthalpy of Vaporization: 48.76 kJ/mol; (21)Boiling Point: 250.4 °C at 760 mmHg; (22)Vapour Pressure: 0.0218 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: Clc1cc(cnc1C#N)C(F)(F)F
(2) InChI: InChI=1/C7H2ClF3N2/c8-5-1-4(7(9,10)11)3-13-6(5)2-12/h1,3H
(3) InChIKey: FUPKVFJSGNZICR-UHFFFAOYAT

Product Name

2-Cyano-3-chloro-5-(trifluoromethyl)-pyridine

Synthetic route

3-Chloro-5-trifluoromethylpyridine-2-carbonitrile Specification

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