5-Indoleboronic acid pinacol ester Chemical Properties

Melting point:

120-125 °C (lit.)

Boiling point:

396.0±15.0 °C(Predicted)

Density 

1.11±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

17.01±0.30(Predicted)

form 

Crystalline Powder

color 

Pale yellow to brown

Water Solubility 

Insoluble

CAS DataBase Reference

269410-24-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36-36/37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

5-Indoleboronic acid pinacol ester Usage And Synthesis

Chemical Properties

Pale yellow to brownish crystalline powder

Uses

Indole-5-boronic acid, pinacol ester

Synthesis

In a 500-mL single-necked flask, 5-bromoindole (20.00 g, 0.1 mol), bis(pinacolato)diboron (51.80 g, 0.2 mol), potassium acetate (22.80 g, 0.2 mol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (1.50 g), and 350 mL of dioxane were added in sequence. The reaction mixture was refluxed for 8 hours under nitrogen protection. After completion of the reaction, it was cooled to room temperature and the dioxane solvent was removed by rotary evaporator. Subsequently, the reaction mixture was washed with 200 ml of distilled water and extracted (3 times) with dichloromethane. The organic phases were combined and recrystallized by methanol-dichloromethane mixed solvent to give 21.8 g of 5-indoleboronic acid pinacol ester in 90% yield.

References

[1] Patent: CN105601612, 2016, A. Location in patent: Paragraph 0051; 0052; 0053
[2] Journal of Organic Chemistry, 2004, vol. 69, # 20, p. 6812 - 6820
[3] Organic Letters, 2012, vol. 14, # 2, p. 600 - 603
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 17, p. 4150 - 4155
[5] Patent: KR101603387, 2016, B1. Location in patent: Paragraph 0084-0088; 0143-0146

5-Indoleboronic acid pinacol ester(269410-24-4)Related Product Information

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