5-Methoxy-2-methyl benzeneboronic acid

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CAS:617689-07-3
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CAS:617689-07-3
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5-Methoxy-2-methyl benzeneboronic acid Basic information
Product Name:5-Methoxy-2-methyl benzeneboronic acid
Synonyms:5-Methoxy-2-methyl benzeneboronic acid;2-Methyl-5-Methoxy-phenylboronic acid;(5-Methoxy-2-methylphenyl);Boronic acid, B-(5-methoxy-2-methylphenyl)-;(5-Methoxy-2-methylphenyl)boronic acid(contains varying amounts of Anhydride);boronic acid, (5-methoxy-2-methylphenyl)-
CAS:617689-07-3
MF:C8H11BO3
MW:165.98
EINECS:
Product Categories:
Mol File:Mol File
5-Methoxy-2-methyl benzeneboronic acid Structure
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
pka8.18±0.58(Predicted)
AppearanceLight brown to brown Solid
Safety Information
HS Code 2931900090
MSDS Information
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
2-BroMo-4-Methoxy-1-Methyl-benzene

36942-56-0

5-Methoxy-2-methyl benzeneboronic acid

617689-07-3

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
5-Methoxy-2-methyl benzeneboronic acid Preparation Products And Raw materials
Raw materials2-BroMo-4-Methoxy-1-Methyl-benzene-->n-Butyllithium-->Trimethyl borate-->Hydrochloric acid
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