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771465

Sigma-Aldrich

3-(Acrylamido)phenylboronic acid

98%

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Synonym(s):
3-(Propenamido)phenylboronic acid, N-Acryloyl-3-aminophenylboronic acid, Boronic acid acrylamide, Phenylboronate acrylamide
Empirical Formula (Hill Notation):
C9H10BNO3
CAS Number:
Molecular Weight:
190.99
MDL number:
PubChem Substance ID:
NACRES:
NA.23

Quality Level

assay

98%

form

powder

mp

129-146 °C

storage temp.

2-8°C

SMILES string

OB(O)c1cccc(NC(=O)C=C)c1

InChI

1S/C9H10BNO3/c1-2-9(12)11-8-5-3-4-7(6-8)10(13)14/h2-6,13-14H,1H2,(H,11,12)

InChI key

ULVXDHIJOKEBMW-UHFFFAOYSA-N

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This Item
436836706086721034
vibrant-m

771465

3-(Acrylamido)phenylboronic acid

vibrant-m

436836

2-Thienylboronic acid

vibrant-m

721034

5-Chloro-3-pyridineboronic acid

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

form

powder

form

solid

form

powder or crystals

form

solid

mp

129-146 °C

mp

138-140 °C (lit.)

mp

100-117 °C

mp

255-260 °C

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

General description

3-(Acrylamido)phenylboronic acid(AAPBA) belongs to the class of boronic acid monomers. The boronic acid group (-B(OH)₂)possesses the unique ability to form reversible covalent bonds with certain molecules, such as diols or sugars. This property allows for the design of molecular sensors for detecting and quantifying specific analytes, including carbohydrates and biomolecules. The acrylamido group provides hydrophilic characteristics, making it more suitable for drug delivery applications. It is also utilized as a building block to synthesize boronic acid-based polymers or copolymers for biomedical engineering, and biosensors for glucose monitoring.

Application

3-(Acrylamido)phenylboronic acid can be used as:
  • As a monomer to synthesize poly(methacrylic acid)-co-3-(acrylamido)phenylboronic acid (PMAA-co-AAPBA) copolymer as a supramolecular receptor for biosensor applications. AAPBA helps to enhance the water solubility and binding affinity of the copolymer. This copolymer is utilized for carbohydrate sensing in an aqueous medium.
  • As a monomer to prepare poly(3-Acrylamidophenyl boronic acid-b-diethylene glycol dimethacrylate) for the fabrication of glucose-sensitive nanoparticles for insulin delivery. The specific interactions of AAPBA with the diol moiety present in glucose molecules induce glucose responsiveness into the block copolymer.
  • As a monomer and cross-linker to synthesize self-healing composite hydrogels for tissue engineering and drug delivery systems. They can mimic the properties of natural tissues and provide a suitable environment for cell growth. AAPBA polymerizes with acrylamide and simultaneously interacts with cis-diol of hydroxypropyl guar gum (HPG) to facilitate the formation of hydrogel with good mechanical strength and fast self-healing properties.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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