Identification | Back Directory | [Name]
5-Methoxy-2-methyl benzeneboronic acid | [CAS]
617689-07-3 | [Synonyms]
(5-Methoxy-2-methylphenyl) 2-Methyl-5-Methoxy-phenylboronic acid 5-Methoxy-2-methyl benzeneboronic acid Boronic acid, B-(5-methoxy-2-methylphenyl)- | [Molecular Formula]
C8H11BO3 | [MDL Number]
MFCD03425973 | [MOL File]
617689-07-3.mol | [Molecular Weight]
165.98 |
Chemical Properties | Back Directory | [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 |
Hazard Information | Back Directory | [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 |
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SynAsst Chemical.
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