5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole Chemical Properties

Melting point:

88-93°C

Boiling point:

350.1±15.0 °C(Predicted)

Density 

1.14±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

0.17±0.10(Predicted)

form 

solid

Appearance

White to yellow Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22

WGK Germany 

3

HS Code 

2934999090

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole Usage And Synthesis

Synthesis

5-Bromobenzoxazole (1 g, 5.05 mmol), pinacol ester of bisboronic acid (1.54 g, 6.06 mmol), potassium acetate (1.49 g, 15.15 mmol) and Pd(dppf)Cl2 (184.76 mg, 0.25 mmol) were used as raw materials, and the above reagents were added to a reaction flask under nitrogen protection, using 1,4-dioxane as solvent. The reaction mixture was stirred at 100 °C for 8 hours. After completion of the reaction, it was cooled to room temperature and the solvent was removed by distillation under reduced pressure. The crude product was purified by column chromatography to afford 1.03 g of the target product benzoxazole-5-boronic acid pinacol ester in white powder form in 83.4% yield.

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6337 - 6352
[2] Patent: CN108503634, 2018, A. Location in patent: Paragraph 0316; 0317; 0320; 0321
[3] Patent: US2016/318895, 2016, A1. Location in patent: Paragraph 0300
[4] Journal of Medicinal Chemistry, 2018, vol. 61, # 23, p. 10724 - 10738
[5] Patent: WO2011/14795, 2011, A2. Location in patent: Page/Page column 94

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