2-Methoxypyridine-3-boronic acid Chemical Properties

Melting point:

140-144 °C

Boiling point:

326.4±52.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

soluble in Methanol

pka

6.90±0.58(Predicted)

form 

Crystalline Powder

color 

White

InChI

InChI=1S/C6H8BNO3/c1-11-6-5(7(9)10)3-2-4-8-6/h2-4,9-10H,1H3

InChIKey

NVOLYUXUHWBCRJ-UHFFFAOYSA-N

SMILES

B(C1=CC=CN=C1OC)(O)O

CAS DataBase Reference

163105-90-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:ALFA

2-Methoxypyridine-3-boronic acid Usage And Synthesis

Chemical Properties

White to light brown powder

Uses

2-Methoxypyridine-3-boronic acid is a biochemical reagent that can be used as a biological material or organic compound for life science related research.

General Description

May contain varying amounts of anhydride.

Synthesis

The general procedure for the synthesis of 2-methoxypyridine-3-boronic acid from 2-methoxypyridine was as follows: 2-methoxypyridine (23.2 g) and diisopropylamine (1.35 mL) were dissolved in tetrahydrofuran (THF, 223 mL) at -20 °C, and lithium (trimethylsilylmethyl) was slowly added (218 mL, 13.8 wt% hexane solution). After 7 hours of reaction, the lithiation was 84% complete. Maintaining a temperature of -20 °C, triisopropyl borate (40.8 g) was added dropwise over 40 min. Subsequently, the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, 5% aqueous sodium hydroxide solution (225 mL) was added for hydrolysis. After separation of the aqueous layer, the pH was adjusted with 10% aqueous hydrochloric acid solution to 5. The resulting white precipitate was collected by filtration. After drying, 22.23 g of 2-methoxypyridine-3-boronic acid was obtained in 68% yield.

References

[1] Patent: WO2004/92125, 2004, A2. Location in patent: Page 8
[2] Journal of Organic Chemistry, 2005, vol. 70, # 1, p. 388 - 390
[3] Synthesis, 2003, # 7, p. 1035 - 1038

2-Methoxypyridine-3-boronic acid(163105-90-6)Related Product Information

• POLY(ETHYLENE GLYCOL) METHYL ETHER ACRYLATE
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• 2-Methoxypyridine
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• Anisole
• Guaiacol
• 2-Picoline
• p-Anisaldehyde
• 4-Methoxybenzyl cyanide
• Citric acid
• Ascoric Acid
• 5-BROMO-2-ETHOXYPYRIDIN-3-YLBORONIC ACID
• 5-Chloro-2-methoxypyridine-3-boronic acid
• 2-BENZYLOXYPYRIDIN-3-YLBORONIC ACID
• 5-Bromo-2-methoxypyridine-3-boronic acid 97%
• 2,6-Dimethoxypyridine-3-boronic acid