(6-Chloro-pyridin-2-yl)-acetonitrile Chemical Properties

Boiling point:

270.7±25.0 °C(Predicted)

Density 

1.262±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

-1.57±0.10(Predicted)

Appearance

Off-white to light yellow Solid

(6-Chloro-pyridin-2-yl)-acetonitrile Usage And Synthesis

Uses

2-(6-Chloropyridin-2-yl)acetonitrile is a useful research chemical used in the cyanomethylation of bromopyridines by nucleophilic substitution with lithioacetonitrile.

Synthesis

Under argon protection, acetonitrile (2.77 mL) was dissolved in tetrahydrofuran (80 mL) and cooled to -78 °C. A hexane solution of n-butyllithium (1.6 M, 29.6 mL) was added slowly and the reaction mixture was stirred at -78 °C for 1 hour. Subsequently, a solution of tetrahydrofuran (10 mL) of 2,6-dichloropyridine (2.0 g) was added dropwise at the same temperature and stirring was continued at -78 °C for 2 hours. Upon completion of the reaction, the mixture was allowed to slowly warm up to room temperature. Water was added to the reaction mixture and extracted with ethyl acetate. The organic phases were combined, washed sequentially with water and saturated saline and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the resulting crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane) to give 6-chloro-2-pyridine acetonitrile (1.91 g). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 3.93 (2H, s), 7.33 (1H, dd, J = 8.1, 0.6 Hz), 7.43 (1H, dd, J = 7.5, 0.6 Hz), 7.73 (1H, t, J = 7.8 Hz).

References

[1] Synlett, 2000, # 10, p. 1488 - 1490
[2] Patent: EP2818473, 2014, A1. Location in patent: Paragraph 0676

(6-Chloro-pyridin-2-yl)-acetonitrile(75279-60-6)Related Product Information

• 6-METHYLPYRIDINE-2-BORONIC ACID
• 2-Pyridineacetic acid, 6-methyl- (9CI)
• 3-Pyridinol,6-chloro-2-methyl-(9CI)
• Trichloroacetonitrile
• 2-[6-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-2-PHENYLACETONITRILE
• 2-(4-CHLOROPHENYL)-2-(6-CHLORO-2-PYRIDINYL)ACETONITRILE
• 2-(6-CHLORO-2-PYRIDINYL)-2-PHENYLACETONITRILE
• (6-Chloro-pyridin-2-yl)-acetonitrile