2-Acrylamidophenylboronic acid

• CAS: 758697-66-4
• Catalog Number: ACM758697664
• Category: Other Products; Main Products
• Molecular Weight: 191.0
• Molecular Formula: C9H10BNO3
• Synonyms: 2-Acrylamidophenylboronic acid, 758697-66-4, ACMC-209p0k, SureCN236887, AGN-PC-0254SH, (2-Acrylamidophenyl)boronic acid, CTK5E2119, ANW-36690, AKOS006346586, AG-I-03294, AK141647, KB-19423, X0983, A-3675, I04-2137, Boronic acid, [2-[(1-oxo-2-propenyl)amino]phenyl]-
• IUPAC Name: [2-(prop-2-enoylamino)phenyl]boronic acid
• SMILES: B(C1=CC=CC=C1NC(=O)C=C)(O)O
• InChI Key: XGDUBFMBDDZYKB-UHFFFAOYSA-N
• Appearance: Solid
• Exact Mass: 191.07500
• H-Bond Acceptor: 3
• H-Bond Donor: 3

Case Study

2-Acrylamidophenylboronic Acid as a Glucose-Sensitive Monomer for Triggered Micellization

Wang, Qingxian, et al. ACS Applied Polymer Materials 2.9 (2020): 3966-3976.

2-Acrylamidophenylboronic acid (2-AAPBA) is a phenylboronic acid (PBA) functional monomer that, when copolymerized with N-isopropylacrylamide (NIPAM), imparts a unique glucose-responsive property to the resulting polymer. Unlike 3-or 4-substituted PBA derivatives, 2-AAPBA enables glucose-induced micellization of block copolymers instead of disassembly.
Fabrication Process: Using a PEG macro-RAFT agent, PEG-b-P(NIPAM-co-2-AAPBA) block copolymers (2-AAPBA content 5-15 mol%) were synthesized by RAFT copolymerization of NIPAM and 2-AAPBA in methanol/water at 70 °C with AIBN initiator. The copolymer was purified by precipitation in diethyl ether.
Performance Evaluation: The P(NIPAM-co-2-AAPBA) block exhibited a lower critical solution temperature (LCST) of ~33 °C. Addition of glucose (100 mM) lowered the LCST to 29 °C, as measured by turbidity. Thus, at 30 °C, glucose triggered the block copolymer to self-assemble into micelles (hydrodynamic radius increased from ~4.7 nm to ~49 nm; transmittance decreased). In contrast, a 3-substituted analogue (3-AAPBA) showed LCST elevation, leading to micelle disassembly. Fructose, mannose, and galactose also induced micellization. MTT assay on L929 cells showed >90% viability at up to 500 μg/mL.
Conclusion: 2-AAPBA enables a reverse glucose-responsive mechanism-glucose lowers LCST and induces micellization-offering a new platform for glucose-triggered drug delivery.

2-Acrylamidophenylboronic Acid as a Dynamic Cross-Linker for Self-Healing Hydrogels at Neutral and Acidic pH

Deng, Christopher C., et al. ACS Macro Letters 4.2 (2015): 220-224.

2-Acrylamidophenylboronic acid (2APBA) is a boronic acid monomer that forms stable boronate ester cross-links with diols even at neutral and acidic pH due to intramolecular B-O coordination between the amide carbonyl and boron. This enables self-healing hydrogels over a broad pH range.
Fabrication Process: Copolymers of 2APBAE (pinacol-protected) with N,N-dimethylacrylamide (DMA) were synthesized by free-radical polymerization, then deprotected to yield P(2APBA-co-DMA). Two diol partners were used: poly(vinyl alcohol) (PVOH) and a catechol-functionalized copolymer P(DOPAAm-co-DMA). Hydrogels formed rapidly (≤1 min) upon mixing 10 wt% aqueous solutions at pH 7.0 or pH 4.0.
Performance Evaluation: Vial inversion confirmed gelation. Cut-and-heal tests showed complete macroscopic healing within 60 min at both pH values; healed gels supported their own weight. Rheology revealed frequency-dependent storage modulus (G' > G'') and rapid modulus recovery after high-strain fracture (400 % strain). PVOH cross-linked gels showed higher equilibrium modulus (~1 kPa) than catechol-based gels (~350 Pa). Catechol oxidation (air exposure, 24 h) initially preserved self-healing but after one week led to loss of creep and healing ability.
Conclusion: 2APBA enables dynamic boronate ester hydrogels with self-healing at neutral and acidic pH, suitable for biomedical applications in physiological and gastrointestinal environments.

2-Acrylamidophenylboronic Acid as a Dynamic Cross-Linker for Self-Healing, Biocompatible Hydrogels

Gosecki, Mateusz, et al. Biomacromolecules 18.10 (2017): 3418-3431.

2-Acrylamidophenylboronic acid (2APBA) is a boronic acid monomer that, when copolymerized with acrylamide, forms a water-soluble polymer capable of reversible cross-linking with hyperbranched polyglycerol (HbPGL) via boronate ester bonds at neutral pH. The resulting hydrogels are injectable, self-healing, and suitable for enzyme-triggered biomineralization.
Fabrication Process: Poly(AM-ran-2APBA) copolymers (6 mol% 2APBA, Mn = 23 kDa or 41 kDa) were mixed with HbPGL (Mn = 6.4 kDa) in PBS (pH 7.4) at total polymer concentrations of 23-30 wt%. Gelation occurred within seconds via boronate ester formation between the diol groups of HbPGL and the boronic acid units.
Performance Evaluation: Rheology showed storage modulus G'> G'' over a broad frequency range; the critical crossover frequency increased from 0.89 to 5.51 rad/s upon raising temperature from 10 to 37 °C, indicating dynamic, reversible cross-links. The hydrogels self-healed within 60 min after cutting. Alkaline phosphatase encapsulated within the gels retained activity (Km increased from 5.76 mM in solution to 7.31-9.65 mM). ¹H HR MAS DOSY NMR revealed faster diffusion of p-nitrophenol in hydrogels with shorter copolymer chains (H3B). Upon addition of naphthyl phosphate calcium salt, CaP biomineralization was confirmed by ³¹P NMR (δ 0.60 ppm), with complete conversion in <110 min for H3B.
Conclusion: 2APBA enables reversible, neutral-pH cross-linking, yielding self-healing hydrogels with tunable diffusivity for controlled biomineralization.

Custom Q&A

What is the molecular formula of 2-Acrylamidophenylboronic acid?

The molecular formula is C9H10BNO3.

What are some synonyms of 2-Acrylamidophenylboronic acid?

Some synonyms include (2-Acrylamidophenyl)boronic acid, [2-(prop-2-enoylamino)phenyl]boronic acid, and 2-Acrylamido-phenylboronic acid.

What is the molecular weight of 2-Acrylamidophenylboronic acid?

The molecular weight is 190.99 g/mol.

When was 2-Acrylamidophenylboronic acid created?

It was created on December 4, 2007.

When was 2-Acrylamidophenylboronic acid last modified?

It was last modified on October 21, 2023.

What is the IUPAC name of 2-Acrylamidophenylboronic acid?

The IUPAC name is [2-(prop-2-enoylamino)phenyl]boronic acid.

What is the InChI code of 2-Acrylamidophenylboronic acid?

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

What is the InChIKey of 2-Acrylamidophenylboronic acid?

The InChIKey is XGDUBFMBDDZYKB-UHFFFAOYSA-N.

What is the canonical SMILES of 2-Acrylamidophenylboronic acid?

The canonical SMILES is B(C1=CC=CC=C1NC(=O)C=C)(O)O.

What is the CAS number of 2-Acrylamidophenylboronic acid?

The CAS number is 758697-66-4.