3-Chloro-5-(trifluoromethyl)pyridine Chemical Properties

Melting point:

131.5 °C

Boiling point:

144°C

Density 

1.416±0.06 g/cm3(Predicted)

refractive index 

1.4460 to 1.4500

Flash point:

54℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

0.52±0.20(Predicted)

Appearance

Colorless to off-white <23°C Solid,>27°C Liquid

InChI

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

InChIKey

OMRCXTBFBBWTDL-UHFFFAOYSA-N

SMILES

C1=NC=C(C(F)(F)F)C=C1Cl

Safety Information

Hazard Codes 

Xi,Xn,T

Risk Statements 

20/21/22-36/37/38-25

Safety Statements 

26-36/37/39-36-45

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT, IRRITANT-HARMFUL

HazardClass 

6.1

PackingGroup 

III

HS Code 

2933399990

3-Chloro-5-(trifluoromethyl)pyridine Usage And Synthesis

Chemical Properties

light yellow crystalline

Uses

3-Chloro-5-(trifluoromethyl)pyridine (3CTFP) is a pyridinium salt that is a byproduct of the production of chlorofluorocarbons. It is used to reduce the level of chlorine in water, and it can be used as a pesticide. 3CTFP is also an anion that can be reduced to form the chloride ion. 3CTFP reacts with nucleophiles such as ammonia or amines, which leads to nucleophilic substitution reactions. This reaction can be reversed by adding acid. The product from this reaction is ammonia gas. 

Synthesis

The general procedure for the synthesis of 3-chloro-5-trifluoromethylpyridine using 2,3-dichloro-5-trifluoromethylpyridine as starting material was as follows: zinc powder (1.18 g, 18.0 mmol) was added to a suspension of 2,3-dichloro-5-trifluoromethylpyridine (2.0 g, 9.30 mmol) in a solvent mixture of 80:20 (v/v) water and acetic acid (5 mL) at 90° C with stirring for 1 hour. Subsequently, zinc powder (1 g, 15.3 mmol) was made up and stirring was continued at 90°C for 15 minutes. After completion of the reaction, the mixture was cooled to room temperature, filtered and the filtrate was washed with dichloromethane. The filtrate was carefully concentrated and the residue was purified by silica gel column chromatography with an elution gradient of 100:0 to 0:100 (v/v) hexane:dichloromethane, resulting in 3-chloro-5-trifluoromethylpyridine as a colorless oil (0.120 g, 7% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 7.93 (s, 1H), 8.78 (s, 2H); GC-MS (EI) analysis showed m/z = 181.0, 183.0 [M].

References

[1] Patent: WO2005/94822, 2005, A1. Location in patent: Page/Page column 28
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 20, p. 7150 - 7163

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