2-(2,4-difluorophenyl)-5-(trifluoroMethyl)pyridine

2-(2,4-difluorophenyl)-5-(trifluoroMethyl)pyridine Property

Melting point:

59.0-62.1°C

Boiling point:

253.4±35.0 °C(Predicted)

Density 

1.364±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

1.48±0.27(Predicted)

form 

crystal

color 

off-white microcrystal

InChI

InChI=1S/C12H6F5N/c13-8-2-3-9(10(14)5-8)11-4-1-7(6-18-11)12(15,16)17/h1-6H

InChIKey

FMKQPMDFNYNYAG-UHFFFAOYSA-N

SMILES

C1(C2=CC=C(F)C=C2F)=NC=C(C(F)(F)F)C=C1

Safety

Risk Statements 

36/38

Safety Statements 

23-26-37-60

TSCA 

No

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

2-(2,4-difluorophenyl)-5-(trifluoroMethyl)pyridine Chemical Properties,Usage,Production

Uses

2-(2,4-Difluorophenyl)-5-(trifluoromethyl)pyridine is a ligand used for the preparation of Ir(III) photocatalysts.

reaction suitability

reaction type: Photocatalysis
reagent type: catalyst

Synthesis

General procedure for the synthesis of 2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine from 2-chloro-5-(trifluoromethyl)pyridine and 2,4-difluorophenylboronic acid: To a 100 mL two-necked round-bottomed flask equipped with a magnetic stirrer were added 2-chloro-5-trifluoromethylpyridine (1 equiv), 2,4-difluorophenylboronic acid (1.2 equiv), triphenylphosphine (0.1 equiv), 2 M aqueous potassium carbonate (2.7 eq.) and ethylene glycol dimethyl ether (0.9 M). The reaction mixture was degassed with argon for 15 minutes. Subsequently, palladium acetate (2.5 mol%) was added to the reaction system and degassing was continued for 15 minutes before sealing the reaction system. The reaction mixture was heated to reflux and the progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent ratio of petroleum ether:ethyl acetate = 90:10). Upon completion of the reaction (usually takes 18-24 hours), the reaction mixture was cooled to room temperature and extracted with dichloromethane (3 x 20 mL). The organic phases were combined, washed sequentially with water (3 × 20 mL) and saturated saline (120 mL), dried over anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure. The crude product was purified by fast column chromatography to afford the target product 2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine.

References

[1] Journal of Organometallic Chemistry, 2015, vol. 776, p. 51 - 59
[2] Journal of Organic Chemistry, 2016, vol. 81, # 16, p. 6988 - 6994
[3] Journal of the American Chemical Society, 2017, vol. 139, # 47, p. 17186 - 17192
[4] Chemistry - A European Journal, 2018, vol. 24, # 44, p. 11314 - 11318