1-(Triisopropylsilyl)pyrrole-3-boronic acid Chemical Properties

Boiling point:

337.9±34.0 °C(Predicted)

Density 

0.96±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

solid

pka

9.41±0.10(Predicted)

color 

White

CAS DataBase Reference

138900-55-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT, KEEP COLD

HS Code 

2933998090

1-(Triisopropylsilyl)pyrrole-3-boronic acid Usage And Synthesis

Synthesis

Step 92b: Synthesis of 1-(triisopropylsilyl)pyrrole-3-boronic acid (Compound 0602-197) To a stirring solution of 3-bromo-1-(triisopropylmethylsilyl)pyrrole (0601-197, 1 g, 3.31 mmol) in anhydrous THF (20 mL) under nitrogen protection, a THF solution of n-butyllithium (2.5 M, 1.58 mL, 3.96 mmol) was slowly added at -78 °C. Maintaining this temperature, stirring was continued for 30 minutes. Subsequently, trimethyl borate (687 mg, 6.6 mmol) was added dropwise to the reaction mixture. The reaction mixture was gradually warmed up to room temperature and stirring was continued for 1 hour. After completion of the reaction, the mixture was diluted with 200 mL of water and extracted with 200 mL of ethyl acetate. The organic phase was washed sequentially with 100 mL of water (twice) and 100 mL of brine and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the crude product 0602-197 (280 mg, 32% yield) was obtained as an oil, which was used directly in the next step of the reaction without further purification.LCMS detection showed a molecular ion peak of 268 [M + 1]+.

References

[1] Tetrahedron, 2004, vol. 60, # 34, p. 7141 - 7146
[2] Patent: WO2010/62559, 2010, A1. Location in patent: Page/Page column 105; 106
[3] Patent: US2013/102595, 2013, A1. Location in patent: Paragraph 0608

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