6-CHLORO-2,2'-BIPYRIDINE Chemical Properties

Melting point:

62℃

Boiling point:

320.6±27.0 °C(Predicted)

Density 

1.245±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

Inert atmosphere,Room Temperature

pka

3.72±0.22(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C10H7ClN2/c11-10-6-3-5-9(13-10)8-4-1-2-7-12-8/h1-7H

InChIKey

XRCUTZKABNKOEY-UHFFFAOYSA-N

SMILES

C1(C2=NC=CC=C2)=NC(Cl)=CC=C1

6-CHLORO-2,2'-BIPYRIDINE Usage And Synthesis

Synthesis

Step 1: 2,6-Dichloropyridine (11) (8.88 g, 60.0 mmol) and 2-(tributylmethylstannyl)pyridine (7.36 g, 20.0 mmol) were dissolved in anhydrous toluene (74 mL) under nitrogen protection. To this solution was added tetrakis(triphenylphosphine)palladium (2.31 g, 2.0 mmol), followed by heating the reaction mixture to reflux and stirring for 11 hours. Upon completion of the reaction, the mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to afford the target product 6-chloro-2,2'-bipyridine (12) (3.9 g, quantitative yield). The structure of the product was confirmed by 1H-NMR (DMSO-d6): δ 7.50-7.53 (m, 1H), 7.59 (d, 1H, J = 8.0 Hz), 7.93-8.05 (m, 2H), 8.30 (d, 1H, J = 8.0 Hz), 8.38 (d, 1H, J = 8.0 Hz), 8.72 (d, 1H, J = 4.4 Hz ).

References

[1] Patent: EP2280000, 2011, A1. Location in patent: Page/Page column 34-35
[2] Patent: US2011/28468, 2011, A1. Location in patent: Page/Page column 22
[3] Organic and Biomolecular Chemistry, 2007, vol. 5, # 9, p. 1397 - 1404

6-CHLORO-2,2'-BIPYRIDINE(13040-77-2)Related Product Information

• 3,5,6-Trichloropyrid
• 4,6'-DICHLORO-2,2'-BIPYRIDINE
• 6,6'-Dichloro-2,2'-bipyridine
• 6-CHLORO-2,2'-BIPYRIDINE
• 6-CHLORO-[2,2']BIPYRIDINYL-5-CARBONITRILE
• 6-CHLORO-2,2'-BIPYRIDINE N'-OXIDE