6-Methylpyridine-3-boronic Acid Chemical Properties

Melting point:

128-130°C

Boiling point:

294.7±42.0 °C(Predicted)

Density 

1.18±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

4.27±0.10(Predicted)

form 

Powder

color 

White to pale brown

Stability:

Hygroscopic

CAS DataBase Reference

659742-21-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

HS Code 

29333990

6-Methylpyridine-3-boronic Acid Usage And Synthesis

Chemical Properties

White to off-white solid

Uses

6-Methylpyridine-3-boronic Acid is used in the preparation of various biologically active compound such as phosphoinositide-3-kinases (PI3K) and c-jun N-terminal kinase (JNK) inhibitors.

Uses

suzuki reaction

Synthesis

General procedure for the synthesis of 6-methyl-3-pyridineboronic acid from 6-methyl-3-pyridinol trifluoromethanesulfonate and bis(pinacolato)diboronate: 6-methyl-3-pyridinol trifluoromethanesulfonate (4.6 mmol) was dissolved in acetonitrile (30 mL) and transferred to a 5 mL microwave reaction tube. To this solution was added 1.5 equivalents of bis(pinacolato)diboron (6.9 mmol; 1.71 g). The mixture was stirred on a magnetic stirrer until complete dissolution. Subsequently, potassium acetate (13.8 mmol; 1.35 g) and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (98 mg, 0.03 mol%) were added to the mixture. The reaction mixture was placed in a microwave reactor and heated at 160°C for 2 x 600 seconds. Upon completion of the reaction (monitored by LC-MS), the acetonitrile was removed by evaporation to give a black solid. The solid was dissolved in DMSO and purified by HPLC to give the final target product 6-methyl-3-pyridineboronic acid (580 mg, 92% yield; 4.2 mmol). Mass spectral data: MH+ = 138.

References

[1] Patent: WO2005/32493, 2005, A2. Location in patent: Page/Page column 40-41
[2] Patent: WO2005/32493, 2005, A2. Location in patent: Page/Page column 40-41

6-Methylpyridine-3-boronic Acid(659742-21-9)Related Product Information

• 6-Methylpyridine-3-boronic Acid
• 2-Trifluoromethyl-5-pyridineboric acid
• 2-Fluoro-6-methylpyridine-3-boronic acid
• 3-Amino-5-bromopyridine
• 2-CHLORO-6-PICOLINE-3-BORONIC ACID
• 2,6-DIMETHYL-PYRIDINE-3-BORONIC ACID
• 6-CHLORO-2-PICOLINE-3-BORONIC ACID
• 2-CHLORO-4-PICOLINE-5-BORONIC ACID
• 4-PICOLINE-5-BORONIC ACID,4-PICOLINE-3-BORONIC ACID
• 2-FLUORO-6-PICOLINE-5-BORONIC ACID
• 2-FLUORO-4-PICOLINE-3-BORONIC ACID
• 2-CHLORO-3-PICOLINE-5-BORONIC ACID
• 6-METHOXY-2-PICOLINE-3-BORONIC ACID
• 2-BROMO-3-PICOLINE-5-BORONIC ACID
• 2-Picoline-3-boronic acid hydrochloride,2-PICOLINE-3-BORONIC ACID HCL
• 2-Picoline-5-boronic acid pinacolate
• 2-FLUORO-5-PICOLINE-3-BORONIC ACID
• 2-PICOLINE-4-BORONIC ACID