3-(N,N-DIMETHYLAMINOCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER Chemical Properties

Boiling point:

406.2±28.0 °C(Predicted)

Density 

1.06±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

-1.28±0.70(Predicted)

form 

solid

color 

White

Safety Information

Hazard Codes 

Xi

Risk Statements 

43

Safety Statements 

36/37

HS Code 

2931900090

3-(N,N-DIMETHYLAMINOCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER Usage And Synthesis

Synthesis

GENERAL STEPS: A mixture of bis(pinacolato)diboron (610 mg, 2.4 mmol), 4-bromo-N,N-dimethylbenzamide (2,500 mg, 2.19 mmol), Pd(dppf)Cl2 (18 mg, 0.02 mmol) and KOAc (320 mg, 3.3 mmol) was dissolved in 1,4-dioxane (18 mL) in. The reaction mixture was heated and stirred at 100 °C for 16 h under nitrogen protection. Upon completion of the reaction, the reaction mixture was filtered and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using CH2Cl2 solution with 0-5% MeOH as eluent to afford the target product 4-(dimethylcarbamoyl)phenylboronic acid pinacol ester (540 mg, 90% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 7.86-7.78 (m, 2H), 7.43-7.36 (m, 2H), 3.11 (s, 3H), 2.97 (s, 3H), 1.35 (s, 12H).

References

[1] Patent: US2014/140956, 2014, A1. Location in patent: Paragraph 0677; 0679
[2] Patent: US2016/376283, 2016, A1. Location in patent: Paragraph 0241; 0243

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