4-AMINOCARBONYLPHENYLBORONIC ACID, PINACOL ESTER Chemical Properties

Melting point:

174.9-180.3 °C

Boiling point:

388.2±25.0 °C(Predicted)

Density 

1.11±0.1 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

15.86±0.50(Predicted)

color 

White

CAS DataBase Reference

179117-44-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HS Code 

2931900090

4-AMINOCARBONYLPHENYLBORONIC ACID, PINACOL ESTER Usage And Synthesis

Synthesis

Under argon protection, 1.4 mg (0.005 mmol) of dichlorobis(trimethylphosphine)nickel (NiCl2(PMe3)2), 77.4 mg (0.5 mmol) of 4-chlorobenzamide, 152 mg (1.0 mmol) of cesium fluoride (CsF), 140 mg (0.55 mmol) of bis(pinacolato)bis(boronic acid) ( B2pin2), 180 mg (1.05 mmol) trimethyl (2,2,5,5-tetrafluoroethoxy) silane (TMSEF), and 0.5 mL 1,4-dioxane. The reaction vessel was sealed and the mixture was stirred and reacted at 100°C for 12 hours. Upon completion of the reaction, the reaction vessel was cooled to room temperature and the reaction was quenched by the addition of 1 mL of saturated aqueous ammonium chloride. The mixture was extracted three times with 8 mL of ethyl acetate and the organic phases were combined. The solvent was removed by distillation under reduced pressure and the residue was purified by silica gel column chromatography (eluent gradient: hexane/chloroform/ethyl acetate = 4:1:0 to 4:1:1) to afford 92 mg (75% yield) of the target product 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide as a white solid.

References

[1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 22, p. 3604 - 3610
[2] Organic Letters, 2011, vol. 13, # 21, p. 5766 - 5769
[3] Patent: JP5699037, 2015, B2. Location in patent: Paragraph 0091; 0092

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