3-Aminophenylboronic acid

• CAS: 30418-59-8
• Catalog Number: ACM30418598-1
• Category: Boro-Amino Acids
• Molecular Weight: 136.95g/mol
• Molecular Formula: C6H8BNO2
• IUPAC Name: (3-aminophenyl)boronic acid
• Canonical SMILES: B(C1=CC(=CC=C1)N)(O)O
• InChI: InChI=1S/C6H8BNO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4,9-10H,8H2
• InChI Key: JMZFEHDNIAQMNB-UHFFFAOYSA-N
• Complexity: 110
• Covalently-Bonded Unit Count: 1
• EC Number: 250-189-0
• Exact Mass: 137.064809g/mol
• Formal Charge: 0
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Heavy Atom Count: 10
• Monoisotopic Mass: 137.064809g/mol
• Rotatable Bond Count: 1

Case Study

3-Aminophenylboronic Acid for the Aqueous Phase Transfer of Oleylamine-Capped Gold Nanoparticles

Karaagac Z, et al. Enzyme and Microbial Technology, 2021, 148, 109810.

3-Aminophenylboronic acid (3-APBA) was employed as an effective hydrophilic ligand to facilitate the aqueous phase transfer of oleylamine-capped gold nanoparticles (OA@Au NPs), addressing common limitations in nanoparticle surface modification strategies. Initially, OA@Au NPs were synthesized via the reduction of HAuCl₄·3H₂O in 1,2,3,4-tetrahydronaphthalene with oleylamine as both the reducing agent and stabilizer. The reaction was carried out at 65 °C for 5 hours, yielding a dark purple product after ethanol-induced precipitation and repeated centrifugation at 10,000 rpm. The purified OA@Au NPs were dispersed in hexane for further processing.
For the phase transfer process, 3-APBA (15 mg) was dissolved in 5 mL tetrahydrofuran (THF) and used as a ligand to modify the nanoparticle surface. A 2 mg/mL OA@Au NP solution was added dropwise to the 3-APBA solution under continuous stirring. The mixture was incubated at 55°C for 6 hours, followed by centrifugation at 10,000 rpm to isolate the resulting 3-APBA-modified Au NPs. The functionalized nanoparticles (3-APBA@Au NPs) were then successfully dispersed in water.

3-Aminophenylboronic Acid for the Synthesis of Albumin- and Mucin-Binding AmB Nanoformulations

Banshoya K, et al. Journal of Drug Delivery Science and Technology, 2023, 90, 105176.

In this study, 3-aminophenylboronic acid (APB) was employed to synthesize a novel amphotericin B (AmB) nanoformulation with enhanced solubility, reduced toxicity, and specific binding to albumin and mucin. The synthetic strategy involved the conjugation of APB to a styrene-maleic acid copolymer (SMA), forming the APB-functionalized polymer (APB-SMA). The APB-SMA was synthesized by reacting styrene-maleic anhydride (SMAnh, 100 mg) with APB (40 mg) and triethylamine (20 µL) in 5 mL of DMF under dark conditions at 60 °C for 72 hours. Post-reaction, the product was washed with diethyl ether and vacuum-dried. Residual anhydride groups were hydrolyzed in NaHCO₃ buffer (0.1 M, pH 8.2), followed by dialysis and lyophilization to yield water-soluble APB-SMA.
Boron content in the resulting polymer, indicative of APB incorporation, was quantified via inductively coupled plasma atomic emission spectroscopy (ICP-AES) using the B 249.773 nm line. This confirmed successful APB conjugation onto the polymer backbone.
Subsequently, APB-SMA was utilized to prepare AmB-loaded nanocomplexes through mixing with varying amounts of AmB (10, 40, or 200 mg) in carbonate-bicarbonate buffer (0.1 M, pH 10.5) and DMSO. The mixtures were stirred at room temperature in the dark for 16 hours, dialyzed extensively, and lyophilized. The resulting formulations-APB-SMA/AmB (100:10), (100:40), and (100:200)-demonstrated APB's experimental utility in facilitating boronic ester-mediated interactions, enabling mucin and albumin affinity for targeted drug delivery.

3-Aminophenylboronic Acid for the Conjugation of BSA-MnO₂ Nanozyme

Ma Y, et al. Microchemical Journal, 2025, 213, 113588.

A 3-aminophenylboronic acid (APBA)-functionalized BSA-MnO₂ nanozyme (APBA@BSA-MnO₂) was synthesized to enhance targeted delivery and bioactivity. The process began with the preparation of BSA-MnO₂ nanoparticles. BSA (62.5 mg) was dissolved in deionized water (25 mL), followed by the addition of MnCl₂·4H₂O (350 μL, 100 mM). After stirring for 3 minutes, NaOH (200 μL, 1.0 M) was added, inducing an immediate orange color shift, indicating nanoparticle formation. Continuous stirring for 6-8 hours deepened the color to dark brown, characteristic of MnO₂ formation. The mixture was dialyzed against deionized water for 48 hours and stored at 4 °C.
Conjugation of APBA was achieved via EDC/NHS-mediated coupling. The BSA-MnO₂ suspension (0.5 mL) in PBS (1.5 mL, pH 7.4) was activated with EDC (1 mg) and NHS (1.5 mg) for 20 minutes. APBA (500 μL, 2.5-3.5 M) was then introduced and incubated at 25 °C for 12 hours under agitation (600 rpm). The final product was purified by centrifugation (12,000 rpm, 20 min) and resuspended in PBS.

Custom Q&A

What is the molecular formula of 3-Aminophenylboronic acid?

The molecular formula of 3-Aminophenylboronic acid is C6H8BNO2.

What is the molecular weight of 3-Aminophenylboronic acid?

The molecular weight of 3-Aminophenylboronic acid is 136.95 g/mol.

What is the IUPAC name of 3-Aminophenylboronic acid?

The IUPAC name of 3-Aminophenylboronic acid is (3-aminophenyl)boronic acid.

What is the InChI of 3-Aminophenylboronic acid?

The InChI of 3-Aminophenylboronic acid is InChI=1S/C6H8BNO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4,9-10H,8H2.

What is the InChIKey of 3-Aminophenylboronic acid?

The InChIKey of 3-Aminophenylboronic acid is JMZFEHDNIAQMNB-UHFFFAOYSA-N.

What is the canonical SMILES of 3-Aminophenylboronic acid?

The canonical SMILES of 3-Aminophenylboronic acid is B(C1=CC(=CC=C1)N)(O)O.

What is the CAS number of 3-Aminophenylboronic acid?

The CAS number of 3-Aminophenylboronic acid is 30418-59-8.

What is the European Community (EC) number of 3-Aminophenylboronic acid?

The European Community (EC) number of 3-Aminophenylboronic acid is 250-189-0.

What is the ChEMBL ID of 3-Aminophenylboronic acid?

The ChEMBL ID of 3-Aminophenylboronic acid is CHEMBL20852.

What is the hydrogen bond donor count of 3-Aminophenylboronic acid?

The hydrogen bond donor count of 3-Aminophenylboronic acid is 3.