5-Methoxy-2-methyl benzeneboronic acid Chemical Properties

Boiling point:

334.9±52.0 °C(Predicted)

Density 

1.14±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

8.18±0.58(Predicted)

Appearance

Light brown to brown Solid

Safety Information

HS Code 

2931900090

5-Methoxy-2-methyl benzeneboronic acid Usage And Synthesis

Uses

(5-Methoxy-2-methylphenyl)boronic Acid is used in preparation of Phenyl-substituted Imidazopyridine Amides useful in the treatment of cardiovascular and other disorders.

Synthesis

The general procedure for the synthesis of 5-methoxy-2-methylphenylboronic acid from 3-bromo-4-methylanisole was as follows: 2.5 M n-butyllithium (nBuLi, 1.8 mL, 4.5 mmol) was added slowly and dropwise over a period of 5 min to 2-bromo-4-methoxy-1-methylbenzene (750 mg, 3.73 mmol) in an anhydrous tetrahydrofuran (THF,) at -78 °C. 30 mL) solution. The reaction mixture was stirred at -78 °C for 20 min before adding anhydrous trimethylborate (0.62 g, 6 mmol). The reaction mixture was warmed to room temperature and kept for 2 hours. The reaction was quenched by addition of 2N hydrochloric acid (HCl, 1 mL). THF was removed by distillation under reduced pressure. the crude product was diluted with 2N HCl (100 mL) and extracted with ethyl acetate (2 x 50 mL). The combined organic phases were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a light yellow solid product (0.43 g, 69% yield).

References

[1] Patent: US2005/245524, 2005, A1. Location in patent: Page/Page column 98-99