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205444-22-0

Basic Information
CAS No.: 205444-22-0
Name: 2-Chloro-4-iodo-6-(trifluoromethyl)pyridine
Article Data: 5
Molecular Structure:
Molecular Structure of 205444-22-0 (2-Chloro-4-iodo-6-(trifluoromethyl)pyridine)
Formula: C6H2ClF3IN
Molecular Weight: 307.441
Synonyms: Pyridine, 2-chloro-4-iodo-6-(trifluoromethyl)-;
Density: 2.047 g/cm3
Melting Point: 94-95℃
Boiling Point: 230.469 °C at 760 mmHg
Flash Point: 93.185 °C
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
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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