N-Boc-indole-2-boronic acid Chemical Properties

Melting point:

84-94 °C 85-90 °C (lit.)

Boiling point:

443.5±55.0 °C(Predicted)

Density 

1.17±0.1 g/cm3(Predicted)

storage temp. 

-20°C

pka

8.12±0.30(Predicted)

form 

powder to crystal

color 

White to Orange to Green

BRN 

8148683

CAS DataBase Reference

213318-44-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-37/39-26

WGK Germany 

3

Hazard Note 

IrritantKeep Cold

HazardClass 

IRRITANT

HS Code 

2933998090

MSDS

• Language:English Provider:ALFA

N-Boc-indole-2-boronic acid Usage And Synthesis

Chemical Properties

White to light yellow crystal powde

Uses

Reactant involved in:

• Suzuki-Miyaura cross-coupling reactions
• Copper-catalyzed trifluoromethylation
• Palladium-catalyzed benzylation
• Homocoupling reactions

General Description

May contain varying amounts of anhydride

Synthesis

Step 2: Synthesis of 1-(tert-butoxycarbonyl)-1H-indole-2-boronic acid Lithium diisopropylammonium (140 mL, 2.0 M in hexane) was slowly added dropwise to a solution of ethoxyethane (500 mL) containing tert-butyl 1H-indole-1-carboxylate (26 g, 119.67 mmol) and triisopropylboronate (30 g, 159.57 mmol) at -70 °C. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent ratio ethyl acetate/petroleum ether = 1:5) during the reaction. Upon completion of the reaction, the reaction was quenched with 200 g of ice-water mixture, followed by adjusting the pH with 10% hydrochloric acid solution to 7. The reaction mixture was extracted with ethyl ether (100 mL x 1), and the organic layers were combined and dried over anhydrous sodium sulfate. Concentration under reduced pressure gave 13 g (67% yield) of the target compound 1-(tert-butoxycarbonyl)-1H-indole-2-boronic acid as a white solid.

References

[1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 8, p. 1218 - 1227
[2] Patent: US2008/139558, 2008, A1. Location in patent: Page/Page column 67
[3] Patent: EP2687530, 2014, A1. Location in patent: Paragraph 0096

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