5-BROMO-2-CHLORO-4,6-DIMETHYLNICOTINONITRILE Chemical Properties

Melting point:

106-108°C

Boiling point:

320.1±37.0 °C(Predicted)

Density 

1?+-.0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

-2.79±0.10(Predicted)

Appearance

Off-white to light yellow Solid

Safety Information

Risk Statements 

20/21/22

Safety Statements 

36/37

HazardClass 

IRRITANT

HS Code 

29269090

5-BROMO-2-CHLORO-4,6-DIMETHYLNICOTINONITRILE Usage And Synthesis

Chemical Properties

Off-white solid

Synthesis

General procedure for the synthesis of 2-chloro-4,6-dimethyl-5-bromonicotinonitrile from 2-hydroxy-3-cyano-4,6-dimethyl-5-bromopyridine: To a solution of 5-chloro-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (14 g, 61.7 mmol) in POCl3 (10 mL) was added phosphorus pentachloride (12.84 g, 61.7 mmol). The reaction mixture was heated to reflux and held for about 8 hours. Upon completion of the reaction, POCl3 was removed by distillation under reduced pressure. the residue was partitioned between dichloromethane (100 mL) and 5% aqueous sodium hydroxide solution (100 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was again dissolved in POCl3 (20 mL) and phosphorus pentachloride (13 g, 62.4 mmol) was added. The reaction mixture was heated to reflux and held for about 12 hours. Upon completion of the reaction, POCl3 was removed by distillation under reduced pressure. the residue was partitioned between dichloromethane (100 mL) and 5% aqueous sodium hydroxide solution (100 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 5-bromo-2-chloro-4,6-dimethylnicotinonitrile (12 g, 79% yield). LCMS (Table 1, method d) retention time = 2.12 min; mass spectrum m/z = 246,248 (M + H).

References

[1] Journal of Organic Chemistry, 1984, vol. 49, # 26, p. 5237 - 5243
[2] Patent: WO2016/198908, 2016, A1. Location in patent: Page/Page column 76
[3] Biological and Pharmaceutical Bulletin, 2016, vol. 39, # 4, p. 473 - 483

5-BROMO-2-CHLORO-4,6-DIMETHYLNICOTINONITRILE(42951-71-3)Related Product Information

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