N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)acetamide

N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)acetamide Property

Boiling point:

441.8±30.0 °C(Predicted)

Density 

1.11±0.1 g/cm3 (20 ºC 760 Torr)

storage temp. 

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

form 

Solid

pka

14.30±0.70(Predicted)

Appearance

White to off-white Solid

CAS DataBase Reference

1201645-46-6

Safety

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)acetamide Chemical Properties,Usage,Production

Synthesis

General procedure: 3-acetamido-5-bromopyridine (0.23 mol, 58.42 g), bis(pinacolato)diboron (0.23 mol, 58.42 g) and potassium acetate (0.69 mol, 67.62 g) were added sequentially to a 1 L four-necked round-bottomed flask equipped with a magnetic stirrer, a thermometer, a reflux condenser and a nitrogen bulb apparatus, followed by 450 mL of dioxane as solvent. Ferrocene palladium chloride (0.0051 mol, 3.80 g) was added to the reaction system as a catalyst under nitrogen protection. The reaction mixture was heated to 100 °C and the reaction was stirred at this temperature for 18-24 h. The progress of the reaction was monitored by thin layer chromatography (TLC) until the reaction was complete. After completion of the reaction, it was cooled to room temperature and the precipitated solid was separated by pulping and filtration. The solid was dissolved in 500 mL of methanol, filtered and the solvent was evaporated to dryness. Finally, heptane was added for pulping to obtain the target product 3-acetamido-pyridine-5-boronic acid pinacol ester 55.40 g in 92.1% yield.

References

[1] Patent: CN103601745, 2017, B. Location in patent: Paragraph 0037; 0038
[2] Patent: WO2014/140077, 2014, A1. Location in patent: Page/Page column 55-56
[3] Patent: WO2009/155527, 2009, A2. Location in patent: Page/Page column 254