2-ETHOXY-3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE Chemical Properties

Boiling point:

344.7±27.0 °C(Predicted)

Density 

1.05±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

4.03±0.24(Predicted)

form 

solid

Appearance

Colorless to light yellow Liquid

CAS DataBase Reference

848243-23-2

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

MSDS

• Language:English Provider:ALFA

2-ETHOXY-3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE Usage And Synthesis

Synthesis

A suspension was prepared in DMSO (100 mL) with 3-bromo-2-ethoxypyridine (28.69 g, 142.0 mmol), bis(pinacolato)diboron (43.3 g, 170.5 mmol) and potassium acetate (41.8 g, 425.9 mmol). The suspension was degassed with nitrogen and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (5.8 g, 7.93 mmol) was added. The reaction mixture was stirred at 95 °C for 6 hours. After completion of the reaction, the reaction mixture was filtered through an Arbocel pad and washed with ethyl acetate (500 mL). The filtrate was concentrated under vacuum and the crude product was purified by silica gel column chromatography using a 50% cyclohexane solution of ethyl acetate as eluent to afford 2-ethoxypyridine-3-boronic acid pinacol ester as a red oil (34.4 g, 74% yield).1H NMR (400 MHz, CDCl3) data were as follows: δ 1.35 (s, 12H), 1.39 (m, 3H). 4.37 (m, 2H), 6.81 (m, 1H), 7.89 (m, 1H), 8.19 (m, 1H).Results of LCMS analysis: retention time (Rt) = 3.27 min, mass spectrum (MS) m/z 250 [MH]+.

References

[1] Patent: WO2013/93688, 2013, A1. Location in patent: Page/Page column 44-45

2-ETHOXY-3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE(848243-23-2)Related Product Information

• Acetyl chloride
• 2-Ethoxy-3-pyridineboronic acid
• 2-Ethoxypyridine
• Pentaborane
• 2-ETHOXY-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE
• 2-(CYCLOPENTYLOXY)-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE
• 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-2-(2,2,2-TRIFLUOROETHOXY)PYRIDINE
• 2-(CYCLOHEXYLOXY)-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE
• 2-ISOPROPOXY-3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE
• 2-ETHOXY-3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE
• 2-BENZYLOXY-3-(4,4,5,5-TETRAMETHYL-[1,3,2]-DIOXABOROLAN-2-YL)PYRIDINE
• 2-PROPOXY-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE
• 2-CYCLOPROPYLMETHOXY-3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE