(3-acrylamidophenyl)boronic acid Chemical Properties

Melting point:

129-146°C

Density 

1.22±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

8.05±0.10(Predicted)

form 

powder to crystal

color 

White to Amber

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HS Code 

2931900090

(3-acrylamidophenyl)boronic acid Usage And Synthesis

Uses

suzuki reaction

Uses

This acrylamide monomer contains a glucose sensitive boronic acid commonly used for intelligent polymers solutions and gels;for drug delivery systems;sensors;actuator systems;and bioreactors.

Synthesis

General procedure for the synthesis of 3-acrylamidophenylboronic acid from 3-aminophenylboronic acid and acryloyl chloride: 3-aminophenylboronic acid (0.566 g, 3.65 mmol) and Na2CO3 (0.67 g, 80.3 mmol) were added to 20 mL of a 1:1 (v/v) solvent mixture of tetrahydrofuran and water and the mixture was cooled to 0 °C. Acryloyl chloride (960 mg, 8.06 mmol) was slowly added dropwise under stirring conditions. After the dropwise addition, the mixture was allowed to warm up naturally to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, 10 mL of water was added to terminate the reaction, followed by extraction of the reaction mixture with ethyl acetate (20 mL x 3). The organic phases were combined, washed with saturated NaCl solution (10 mL) and finally the organic layer was dried with anhydrous Na2SO4. After concentrating the organic layer, it was purified by column chromatography to give the light yellow solid product 3-acrylamidophenylboronic acid (0.32 g, 40.1% yield).

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 11, p. 4636 - 4656
[2] Soft Matter, 2014, vol. 10, # 6, p. 911 - 920
[3] Journal of the American Chemical Society, 2011, vol. 133, # 49, p. 19832 - 19838
[4] Patent: CN104945411, 2018, B. Location in patent: Paragraph 0077; 0078; 0079
[5] New Journal of Chemistry, 2012, vol. 36, # 2, p. 438 - 451

(3-acrylamidophenyl)boronic acid(99349-68-5)Related Product Information

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