4-Acetamidophenylboronic acid Chemical Properties

Melting point:

215-220 °C (lit.)

Density 

1.23±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

8.63±0.10(Predicted)

form 

Powder

color 

Gray-tan

Water Solubility 

85 g/L (70 ºC)

CAS DataBase Reference

101251-09-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29319090

MSDS

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

4-Acetamidophenylboronic acid Usage And Synthesis

Chemical Properties

White to light yellow crystal powde

Uses

Reactant involved in:

• Synthesis of TpI2 kinase inhibitors
• Biological evaluation of modulators of survival motor neuron protein
• Cross-coupling with conjugated dienes or terminal alkenes or diazoesters
• Synthesis of tetrabutylammonium trifluoroborates
• Rhosium-catalyzed cyanation

Uses

4-Acetamidophenylboronic Acid is used in the synthesis of potent chrom-4-one inhibitors of the DNA-Dependant protein kinase for use in radiotherapy and chemotherapy in cancer treatment.

Synthesis

To a three-neck flask was added 13.7 g (0.1 mol) of 4-aminophenylboronic acid and 100 mL of trichloromethane. After thorough stirring, the reaction mixture was cooled to 5 °C and then 23.4 g (0.3 mol) of acetyl chloride was added slowly dropwise. After maintaining the reaction temperature at 5°C to complete the dropwise addition, the reaction system was warmed to 40°C and the reaction continued to be stirred for 3 hours. Upon completion of the reaction, 150 mL of water was added to the reaction mixture and the resulting solid product was washed with stirring. Subsequently, the solid was separated by filtration and washed with an appropriate amount of cold water. Finally, the resulting solid was dried in a vacuum drying oven to obtain 14 g of white or off-white solid powder 4-acetylaminophenylboronic acid in 78.2% yield.

References

[1] Patent: CN106946920, 2017, A. Location in patent: Paragraph 0017; 0018; 0020

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