2-Chloro-4-iodo-6-(trifluoromethyl)pyridine supplier

Name
2-Chloro-4-iodo-6-(trifluoromethyl)pyridine
EINECS
CAS No. 205444-22-0
Article Data5
CAS DataBase
Density 2.047 g/cm³
Solubility
Melting Point 94-95℃
Formula C₆H₂ClF₃IN
Boiling Point 230.469 °C at 760 mmHg
Molecular Weight 307.441
Flash Point 93.185 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Pyridine, 2-chloro-4-iodo-6-(trifluoromethyl)-;
PSA 12.89000
LogP 3.35840

Synthetic route

: 39890-95-4
2-chloro-6-trifluoromethylpyridine

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
With n-butyllithium; iodine; diisopropylamine In tetrahydrofuran; hexane 1.) -100 deg C, 2 h; 2.) -100 -> -80 deg C, 30 min;	92%
Stage #1: 2-chloro-6-trifluoromethylpyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -100℃; for 2h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #3: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 3h; Inert atmosphere;	42%
Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere View Scheme

: 205240-59-1
2-chloro-3-iodo-6-(trifluoromethyl)pyridine

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
Stage #1: 2-chloro-3-iodo-6-(trifluoromethyl)pyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -75℃; for 0.75h; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane at 25℃; Further stages.;	83%
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;	81%

: 945717-57-7
6-chloro-3-iodo-2-(trifluoromethyl)pyridine

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -75 - -72℃; for 1.83333h;	69%

: 6322-49-2
4-chloro-2-butanone

: 2-(3-methyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)-N-(6'-methyl-5'-(trifluoromethyl)-[2,3-bipyridin]-6-yl)acetamide

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	11 mg

: 39890-95-4
2-chloro-6-trifluoromethylpyridine

A: 945717-57-7
6-chloro-3-iodo-2-(trifluoromethyl)pyridine

B: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
Stage #1: 2-chloro-6-trifluoromethylpyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -100℃; for 2h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; hexane at -78℃; for 1h;

: 885693-20-9
5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: C16H18ClF3N2O2

Conditions

Conditions	Yield
With potassium phosphate; trans-diacetylpalladium(II) bis(dicyclohexylamine) In ethanol at 20℃; for 18h; Inert atmosphere;	93%
With potassium phosphate; trans-diacetylpalladium(II) bis(dicyclohexylamine) In ethanol at 20℃; for 18h; Suzuki Coupling; Inert atmosphere;	93%

: 1765-93-1
4-fluoroboronic acid

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: 2-chloro-4-(4-fluorophenyl)-6-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water for 1.5h; Reflux;	90%

: 75-77-4
chloro-trimethyl-silane

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: 2-Chloro-4-iodo-6-trifluoromethyl-3-trimethylsilanyl-pyridine

Conditions

Conditions	Yield
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -75℃;	86%

: 2393-23-9
4-methoxy-benzylamine

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: 2-chloro-N-[(4-methoxyphenyl)methyl]-6-(trifluoromethyl)pyridin-4-amine

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In toluene at 100℃; for 3h; Inert atmosphere;	82.51%

: 124-38-9
carbon dioxide

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: 2-chloro-6-(trifluoromethyl)pyridine-4-carboxylic acid

Conditions

Conditions	Yield
Stage #1: 2-chloro-4-iodo-6-(trifluoromethyl)pyridine With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane at 0℃; for 0.0833333h; Stage #2: carbon dioxide In tetrahydrofuran; hexane Stage #3: With hydrogenchloride In tetrahydrofuran; hexane Further stages.;	74%
Stage #1: 2-chloro-4-iodo-6-(trifluoromethyl)pyridine With n-butyllithium In tetrahydrofuran; hexane at -75 - -72℃; for 0.333333h; Stage #2: carbon dioxide In tetrahydrofuran; hexane at 20℃;	56%

: C10H18INO2Zn

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: C16H20ClF3N2O2

Conditions

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0) In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	70%

: C11H20NO2Zn(1+)*I(1-)

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: C17H22ClF3N2O2

Conditions

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0) at 20℃; for 1h; Inert atmosphere; Reflux;	69%

: 67-64-1
acetone

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: 1379375-72-0
2-[2-chloro-6-(trifluoromethyl)pyridin-4-yl]propan-2-ol

Conditions

Conditions	Yield
Stage #1: 2-chloro-4-iodo-6-(trifluoromethyl)pyridine With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.666667h; Inert atmosphere; Stage #2: acetone In tetrahydrofuran at 20℃; for 2h;	65%

: C14H23N3O

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: C20H24ClF3N4O

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; DavePhos In 1,4-dioxane at 100℃; Inert atmosphere; Sealed tube;	65%

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: 2-chloro-6-(trifluoromethyl)isonicotinonitrile

Conditions

Conditions	Yield
With copper(l) cyanide In 1-methyl-pyrrolidin-2-one at 120℃; for 0.166667h; sealed vessel;	64%

: 81500-92-7
3,5-Bis-trimethylsilyl-bromobenzene

: 73183-34-3
bis(pinacol)diborane

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: 4-(3,5-bis(trimethylsilyl)phenyl)-2-chloro-6-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
Stage #1: 3,5-Bis-trimethylsilyl-bromobenzene; bis(pinacol)diborane With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; tricyclohexylphosphine In 1,4-dioxane at 100 - 110℃; for 2h; Inert atmosphere; Stage #2: 2-chloro-4-iodo-6-(trifluoromethyl)pyridine With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water for 0.5h; Reflux;	60%

...Expand

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: 2-Chloro-3,4-diiodo-6-trifluoromethyl-pyridine

Conditions

Conditions	Yield
With n-butyllithium; iodine; diisopropylamine In tetrahydrofuran; hexane at -75℃;	59%

: 85275-45-2
N-tert-butoxycarbonyl-3-piperidinol

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: C16H20ClF3N2O3

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 16h;	59%
Stage #1: N-tert-butoxycarbonyl-3-piperidinol With sodium hydride In N,N-dimethyl-formamide; mineral oil at -40℃; for 0.5h; Stage #2: 2-chloro-4-iodo-6-(trifluoromethyl)pyridine In N,N-dimethyl-formamide; mineral oil at -40 - 20℃; for 16h;	59%

: (±)-tert-butyl 2,7-diazaspiro[4.4]nonane-2-carboxylate

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: tert-Butyl 7-(2-Chloro-6-(trifluoromethyl)pyridin-4-yl)-2,7-diazaspiro[4.4]nonane-2-carboxylate

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In toluene at 100℃; for 16h; Sealed tube; Inert atmosphere;	53%

: 423-39-2
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

: allyl 1-methyl-1H-indole-3-carboxylate

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: (S)-2-(2-chloro-6-(trifluoromethyl)pyridin-4-yl)-4,4,5,5,6,6,7,7,7-nonafluoroheptyl 1-methyl-1H-indole-3-carboxylate

Conditions

Conditions	Yield
Stage #1: allyl 1-methyl-1H-indole-3-carboxylate; 2-chloro-4-iodo-6-(trifluoromethyl)pyridine With manganese; (1,2-dimethoxyethane)dichloronickel(II); (4R,4'R)-4,4'-di(heptan-4-yl)-4,4',5,5'-tetrahydro-2,2'-bioxazole In 1,2-dimethoxyethane for 0.5h; Inert atmosphere; Stage #2: 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane With chloro-trimethyl-silane In 1,2-dimethoxyethane at -10℃; for 24h; Inert atmosphere; enantioselective reaction;	50%

Yield

Stage #1: allyl 1-methyl-1H-indole-3-carboxylate; 2-chloro-4-iodo-6-(trifluoromethyl)pyridine With manganese; (1,2-dimethoxyethane)dichloronickel(II); (4R,4'R)-4,4'-di(heptan-4-yl)-4,4',5,5'-tetrahydro-2,2'-bioxazole In 1,2-dimethoxyethane for 0.5h; Inert atmosphere;
Stage #2: 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane With chloro-trimethyl-silane In 1,2-dimethoxyethane at -10℃; for 24h; Inert atmosphere; enantioselective reaction;

50%

...Expand

: C10H18INO2Zn

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: C16H20ClF3N2O2

Conditions

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0) In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	39%

: 6704-31-0
oxetan-3-one

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: 3-[2-chloro-6-(trifluoromethyl)pyridin-4-yl]oxetan-3-ol

Conditions

Conditions	Yield
Stage #1: 2-chloro-4-iodo-6-(trifluoromethyl)pyridine With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: oxetan-3-one In tetrahydrofuran for 1h;	38%

: (S)-N-(4-cyanophenethyl)pyrrolidine-2-carboxamide hydrochloride

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: (S)-N-(4-cyanophenethyl)-1-(4-iodo-6-(trifluoromethyl)pyridin-2-yl)pyrrolidine-2-carboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 95℃; for 96h;	30%

: 5763-61-1
3,4-dimethoxybenzylamine

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: N-(3,4-dimethoxybenzyl)-4-iodo-6-(trifluoromethyl)pyridin-2-amine

Conditions

Conditions	Yield
With triethylamine In 1-methyl-pyrrolidin-2-one at 100℃; for 0.333333h; Inert atmosphere; Microwave irradiation;	28%

: copper(l) cyanide

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: 2-chloro-6-(trifluoromethyl)isonicotinamide

Conditions

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 120℃; for 3h; Inert atmosphere;	7%

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: 1379376-03-0
tert-butyl 4-{[4-(aminocarbonyl)-6-(trifluoromethyl)pyridin-2-yl]oxy}piperidine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(l) cyanide / 1-methyl-pyrrolidin-2-one / 0.17 h / 120 °C / sealed vessel 2: sodium hydride / tetrahydrofuran; mineral oil / 0.75 h View Scheme

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: 1379376-04-1
2-(piperidin-4-yloxy)-6-(trifluoromethyl)isonicotinamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: copper(l) cyanide / 1-methyl-pyrrolidin-2-one / 0.17 h / 120 °C / sealed vessel 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.75 h 3.1: hydrogenchloride / 1,4-dioxane / 2.5 h 3.2: pH 11 View Scheme

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: 2-[(1-{cis-3-(cyanomethyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutyl}piperidin-4-yl)oxy]-6-(trifluoromethyl)isonicotinamide

: 2-[(1-{trans-3-(cyanomethyl)-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutyl}piperidin-4-yl)oxy]-6-(trifluoromethyl)isonicotinamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: copper(l) cyanide / 1-methyl-pyrrolidin-2-one / 0.17 h / 120 °C / sealed vessel 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.75 h 3.1: hydrogenchloride / 1,4-dioxane / 2.5 h 3.2: pH 11 4.1: sodium cyanoborohydride; zinc(II) chloride / methanol View Scheme

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: 2-[(1-{cis-3-(cyanomethyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutyl}piperidin-4-yl)oxy]-6-(trifluoromethyl)isonicotinonitrile

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: copper(l) cyanide / 1-methyl-pyrrolidin-2-one / 0.17 h / 120 °C / sealed vessel 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.75 h 3.1: hydrogenchloride / 1,4-dioxane / 2.5 h 3.2: pH 11 4.1: sodium cyanoborohydride; zinc(II) chloride / methanol 5.1: triethylamine; trichloroacetic acid anhydride / dichloromethane / 0.42 h / 0 °C 5.2: 1 h View Scheme

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: {cis-3-(4-{[4-(2-hydroxyethyl)-6-(trifluoromethyl)pyridin-2-yl]amino}piperidin-1-yl)-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutyl}acetonitrile

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C 1.2: 1.5 h / -78 - 20 °C 2.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 3.33 h / 100 - 140 °C / Microwave irradiation 3.1: sodium cyanoborohydride; zinc(II) chloride / methanol / 1.33 h 4.1: trifluoroacetic acid / dichloromethane / 1 h View Scheme

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: {trans-3-(4-{[4-(2-hydroxyethyl)-6-(trifluoromethyl)pyridin-2-yl]amino}piperidin-1-yl)-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutyl}acetonitrile

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C 1.2: 1.5 h / -78 - 20 °C 2.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 3.33 h / 100 - 140 °C / Microwave irradiation 3.1: sodium cyanoborohydride; zinc(II) chloride / methanol / 1.33 h 4.1: trifluoroacetic acid / dichloromethane / 1 h View Scheme

: 205444-22-0
2-chloro-4-iodo-6-(trifluoromethyl)pyridine

: 2-[2-(piperidin-4-ylamino)-6-(trifluoromethyl)pyridin-4-yl]ethanol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C 1.2: 1.5 h / -78 - 20 °C 2.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 3.33 h / 100 - 140 °C / Microwave irradiation View Scheme

2-Chloro-4-iodo-6-(trifluoromethyl)pyridine Specification

The systematic name of 2-Chloro-4-iodo-6-(trifluoromethyl)pyridine is 2-chloro-4-iodo-6-(trifluoromethyl)pyridine. With the CAS registry number 205444-22-0, it is also named as Pyridine, 2-chloro-4-iodo-6-(trifluoromethyl)-. In addition, its molecular formula is C₆H₂ClF₃IN and molecular weight is 307.4395.

The other characteristics of 2-Chloro-4-iodo-6-(trifluoromethyl)pyridine can be summarized as: (1)ACD/LogP: 3.35; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3; (4)ACD/LogD (pH 7.4): 3; (5)ACD/BCF (pH 5.5): 101; (6)ACD/BCF (pH 7.4): 101; (7)ACD/KOC (pH 5.5): 947; (8)ACD/KOC (pH 7.4): 947; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 12.89 Å²; (13)Index of Refraction: 1.54; (14)Molar Refractivity: 47.126 cm³; (15)Molar Volume: 150.191 cm³; (16)Polarizability: 18.682×10^-24cm³; (17)Surface Tension: 36.875 dyne/cm; (18)Density: 2.047 g/cm³; (19)Flash Point: 93.185 °C; (20)Enthalpy of Vaporization: 44.813 kJ/mol; (21)Boiling Point: 230.469 °C at 760 mmHg; (22)Vapour Pressure: 0.1 mmHg at 25 °C.

People can use the following data to convert to the molecule structure.
(1)SMILES: Ic1cc(nc(Cl)c1)C(F)(F)F
(2)InChI: InChI=1/C6H2ClF3IN/c7-5-2-3(11)1-4(12-5)6(8,9)10/h1-2H
(3)InChIKey: JHKQSKCFLAXPKK-UHFFFAOYAF
(4)Std. InChI: InChI=1S/C6H2ClF3IN/c7-5-2-3(11)1-4(12-5)6(8,9)10/h1-2H
(5)Std. InChIKey: JHKQSKCFLAXPKK-UHFFFAOYSA-N

Product Name

2-Chloro-4-iodo-6-(trifluoromethyl)pyridine

Synthetic route

2-Chloro-4-iodo-6-(trifluoromethyl)pyridine Specification

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