6-(Morpholin-4-yl)pyridine-3-boronic acid pinacol ester Chemical Properties

Melting point:

135-139 °C (lit.)

Boiling point:

440.9±45.0 °C(Predicted)

Density 

1.13±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

5.58±0.10(Predicted)

Appearance

White to off-white Solid

CAS DataBase Reference

485799-04-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

22-24/25-45-43A-36/37/39-26

RIDADR 

2811

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2934999090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

6-(Morpholin-4-yl)pyridine-3-boronic acid pinacol ester Usage And Synthesis

Uses

6-(morpholino-4-yl)pyridine-3-boronic acid pinacol ester, also known as 6-(4-morpholino)pyridine-3-boronic acid pinacol ester, is an important pharmaceutical and chemical intermediate.

Synthesis

Pinacol ester of bisboronic acid (1.25 g, 4.92 mmol) was dissolved in DMF (10 mL) under nitrogen protection and cooled to 0 °C. KOAc (1.21 g, 12.3 mmol) and Pd(dppf)Cl2-CH2Cl2 (0.1 g, 0.123 mmol) were added sequentially. The reaction mixture was heated to 80 °C and a solution of 5-bromo-2-morpholine pyridine (1.0 g, 4.1 mmol) in DMF (10 mL) was added dropwise. After the dropwise addition, the reaction was continued to be stirred at 80 °C for 10 hours. After completion of the reaction, the solvent was removed by evaporation. The residue was dissolved in ethyl acetate and the insoluble material was removed by filtration. The filtrate was evaporated and purified by column chromatography (eluent ratio: ethyl acetate:petroleum ether = 1:4) to afford 6-(morpholin-4-yl)pyridine-3-boronic acid pinacol ester (940 mg, 79% yield).

References

[1] Patent: WO2008/88881, 2008, A1. Location in patent: Page/Page column 41-42
[2] Patent: WO2009/155527, 2009, A2. Location in patent: Page/Page column 136

6-(Morpholin-4-yl)pyridine-3-boronic acid pinacol ester(485799-04-0)Related Product Information

• Moroxydine hydrochloride
• Tris(trimethylsilyl)phosphate
• Moroxydine
• Methyl acrylate
• Tridemorph
• Pyridine
• BUTYL OLEATE
• Dimethomorph
• morpholine
• 4-[3-METHYL-5-(4,4,5,5-TETRAMETHYL-[1,3,2]-DIOXABOROLAN-2-YL)PYRIDIN-2-YL]MORPHOLINE
• 6-(4-morpholinyl)-3-pyridinylboronic acid
• Borane morpholine complex
• 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• 2-(Dimethylamino)pyridine-5-boronic acid hydrate
• 2-Aminopyridine-5-boronic acid, pinacol ester
• Pentaborane
• 3-Pyridylboronic acid
• (6-AMINOPYRIDIN-3-YL)BORONIC ACID