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2-Methoxy-4-methyl-pyridine-5-boronic acid

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2-Methoxy-4-methyl-pyridine-5-boronic acid Basic information
Product Name:2-Methoxy-4-methyl-pyridine-5-boronic acid
Synonyms:2-METHOXY-4-METHYL-5-PYRIDINYLBORONIC ACID;2-METHOXY-4-PICOLINE-5-BORONIC ACID;6-Methoxy-4-methylpyridine-3-boronic acid;Boronic acid, (6-methoxy-4-methyl-3-pyridinyl)- (9CI);6-METHOXY-4-METHYLPYRIDINE-5-BORONIC ACID;6-Methoxy-4-methylpyridin-3-ylboronic acid;2-Methoxy-4-Methyl-Pyridinyl-5-Boronic Acid;Boronic acid, B-(6-methoxy-4-methyl-3-pyridinyl)-
CAS:503184-35-8
MF:C7H10BNO3
MW:166.97
EINECS:
Product Categories:Pyridines;METHOXY;Pyridine
Mol File:503184-35-8.mol
2-Methoxy-4-methyl-pyridine-5-boronic acid Structure
2-Methoxy-4-methyl-pyridine-5-boronic acid Chemical Properties
Boiling point 339.2±52.0 °C(Predicted)
density 1.20±0.1 g/cm3(Predicted)
storage temp. Inert atmosphere,Store in freezer, under -20°C
pka7.34±0.58(Predicted)
AppearanceWhite to off-white Solid
Safety Information
Hazard Codes Xi
Risk Statements 37/38-41
Safety Statements 26-39
HS Code 2933399990
MSDS Information
2-Methoxy-4-methyl-pyridine-5-boronic acid Usage And Synthesis
Synthesis
5-Bromo-2-methoxy-4-methylpyridine

164513-39-7

2-METHOXY-4-METHYL-PYRIDINE-5-BORONIC ACID

503184-35-8

Under argon protection, butyl lithium solution (1.6 M in hexane, 15.3 mL, 22.27 mmol) was slowly added dropwise to a solution of 5-bromo-2-methoxy-4-methylpyridine (4.5 g, 22.3 mmol) dissolved in 150 mL of tetrahydrofuran, keeping the reaction temperature at -78 °C. After the reaction mixture was stirred continuously at -78 °C for 1 h, triisopropyl borate (6.2 mL, 26.7 mmol) was added. Subsequently, the reaction system was slowly warmed to room temperature and stirring was continued overnight. Upon completion of the reaction, the mixture was poured into a mixture of equal volumes of saturated aqueous ammonium chloride solution and water and extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated. The crude product was washed with ethyl ether to afford 6-methoxy-4-methylpyridine-3-boronic acid as a white solid (2.12 g, 56.6% yield).LRMS (m/z): 168 (M + 1)+.

References[1] Bioorganic and medicinal chemistry letters, 2003, vol. 13, # 2, p. 289 - 291
[2] Patent: EP2738172, 2014, A1. Location in patent: Paragraph 0107
2-Methoxy-4-methyl-pyridine-5-boronic acid Preparation Products And Raw materials
Raw materials5-Bromo-2-methoxy-4-methylpyridine-->Tetrahydrofuran-->n-Butyllithium-->Triisopropyl borate-->Hexane
Tag:2-Methoxy-4-methyl-pyridine-5-boronic acid(503184-35-8) Related Product Information
2-Methoxy-4-methyl-3-nitropyridine-5-boronic acid pinacol ester 2-Methyl-6-methoxypyridine-3-boronic acid 2-Ethoxy-4-methyl-5-pyridinylboronic acid 6-Hydroxy-3-pyridineboronic acid 2-Methoxy-4-methyl-pyridine-5-boronic acid 2-Methoxy-4-methylpyridine 2-Methoxy-5-methylpyridin-3-ylboronic acid 2-Methoxy-5-pyridineboronic acid 4-Methylpyridine-3-boronic acid