3-Bromo-2-methoxypyridine Chemical Properties

Boiling point:

87 °C(Press: 16 Torr)

Density 

1.5856 g/mL at 25 °C

refractive index 

1.566

Flash point:

93 °C

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

pka

1.04±0.10(Predicted)

form 

clear liquid

color 

Colorless to Light yellow

Water Solubility 

Not miscible or difficult to mix in water.

Sensitive 

Moisture Sensitive/Light Sensitive

InChIKey

PORGLLGXCAQORO-UHFFFAOYSA-N

CAS DataBase Reference

13472-59-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-36/37/39

WGK Germany 

3

HS Code 

29333990

3-Bromo-2-methoxypyridine Usage And Synthesis

Uses

It is employed in the facile synthesis of 2-unsubstituted benzofuran-3-carboxylates using diazo(trimethylsilyl)methyl magnesium bromide.

Synthesis

A) 3-bromo-2-chloropyridine (4.76 g) was dissolved in N,N-dimethylformamide (DMF, 30 mL) under argon protection. Subsequently, a methanolic solution of 28% sodium methanol (5.73 g) was added to this solution. The reaction mixture was stirred at 80°C for 30 minutes. After completion of the reaction, the mixture was cooled to room temperature and the reaction was quenched by the addition of water. The reaction mixture was extracted with ethyl acetate and the organic phases were combined. The organic phase was washed sequentially with water and saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to give the crude product 3-bromo-2-methoxypyridine (4.43 g) as a light yellow oil.

References

[1] Patent: EP2816023, 2014, A1. Location in patent: Paragraph 0393; 0394

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