2-Chloro-3-(trifluoromethyl)pyridine Chemical Properties

Melting point:

36-40 °C(lit.)

Boiling point:

166-168°C

Density 

1.416±0.06 g/cm3(Predicted)

Flash point:

180 °F

storage temp. 

Storage temp. 2-8°C

solubility 

soluble in Methanol

pka

-1.68±0.10(Predicted)

form 

Crystals

color 

Semi-transparent

BRN 

4179716

InChI

InChI=1S/C6H3ClF3N/c7-5-4(6(8,9)10)2-1-3-11-5/h1-3H

InChIKey

RXATZPCCMYMPME-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC=C1C(F)(F)F

CAS DataBase Reference

65753-47-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

F,T,Xi

Risk Statements 

11-25-36/37/38-52/53-48/25-34-24/25

Safety Statements 

16-22-36/37/39-45-61-26-23

RIDADR 

UN 2926 4.1/PG 2

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Chloro-3-(trifluoromethyl)pyridine Usage And Synthesis

Chemical Properties

semi-transparent crystals

Uses

2-Chloro-3-(trifluoromethyl)pyridine may be used in the preparation of 5,5′-bis(trifluoromethyl)-2,2′-bipyridine, via modified Ullmann reaction.

General Description

2-Chloro-3-(trifluoromethyl)pyridine is a trifluoromethyl-substituted pyridine derivative.

Synthesis

In a four-necked flask equipped with a stirrer, thermometer and a drying tube, 32.62 g of 3-trifluoromethylpyridine N-oxide (CAS: 22253-72-1) and 46.0 g of phosphorus trichloride were added. The reaction mixture was stirred at 105-110°C for 2 hours. Subsequently, the temperature was raised to 120-125°C and the reaction was continued for 5 hours. The reaction mixture was analyzed by liquid chromatography and confirmed to contain 0.16% of 3-trifluoromethylpyridine N-oxide, 50.34% of 2-chloro-3-trifluoromethylpyridine and 25.34% of 2-chloro-5-trifluoromethylpyridine. The reaction mixture was heated under reduced pressure (100 mmHg) until an internal temperature of 75°C was reached to remove excess TCPO by distillation. The reaction mixture was slowly added to 163.1 g of ice water at a controlled temperature not exceeding 30°C and stirred for 1 hour. The reaction mixture was extracted with 1,2-dichloroethane, stirred for 30 minutes and partitioned. The organic layer was washed with water to give 132.11 g of a 1,2-dichloroethane solution containing 2-chloro-3-trifluoromethylpyridine. Liquid chromatographic analysis showed that the solution contained 13.17 g of 2-chloro-3-trifluoromethylpyridine.

References

[1] Patent: US2012/259125, 2012, A1. Location in patent: Page/Page column 3

2-Chloro-3-(trifluoromethyl)pyridine(65753-47-1)Related Product Information

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