2-Chloro-6-cyanopyridine Chemical Properties

Melting point:

85-89 °C

Boiling point:

245.3±20.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder

pka

-5.77±0.10(Predicted)

color 

White

InChI

InChI=1S/C6H3ClN2/c7-6-3-1-2-5(4-8)9-6/h1-3H

InChIKey

PGZHSVWXFKKCNR-UHFFFAOYSA-N

SMILES

C1(C#N)=NC(Cl)=CC=C1

CAS DataBase Reference

33252-29-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,T,Xi

Risk Statements 

22-37/38-41-36/37/38

Safety Statements 

26-36/37/39-37

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

2-Chloro-6-cyanopyridine Usage And Synthesis

Chemical Properties

Off-white Cryst

Uses

Substrate used in a Negishi coupling reaction with an arylzinc halide catalyzed by Pd-NHC (PEPPSI-Ipr, Catalog No. 668032).

Synthesis

The reaction was carried out with 2-chloro-6-(methylsulfonyl)pyridine (13.0 g, 67.8 mmol) and sodium cyanide (6.69 g, 136 mmol) in DMF (150 ml) with stirring at 170°C for 18 hours. After completion of the reaction, the mixture was cooled to room temperature, poured into water and extracted with ethyl acetate. The organic phases were combined, washed with saturated brine 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 with the eluent petroleum ether-ethyl acetate (2:1, v/v) to afford 2-chloro-6-cyanopyridine (6.67 g, 71% yield) as white crystals with a melting point of 82.9-83.1 °C. IR (KBr, cm-1): 2253 (CN), 1572, 1431, 1161. 1143, 912, 854, 744. 1H-NMR (CDCl3, δ): 7.57 (1H, d, J = 8.0 Hz), 7.65 (1H, d, J = 8.1 Hz), 7.82 (1H, t, J = 7.8 Hz).

References

[1] Patent: EP1424336, 2004, A1. Location in patent: Page 41

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