3-Acrylamidophenylboronic Acid (contains varying amounts of Anhydride) - ≥97% , CAS No.99349-68-5

CAS: 99349-68-5 Cat. No.: A188951 Molecular Weight: 190.99 EC Number: 690-696-8

GRADE & PURITY ≥97%

Synonyms

A846009 | AC-30997 | [3-(prop-2-enamido)phenyl]boronic acid | SCHEMBL235432 | 3-Acrylamidobenzeneboronic Acid | DTXSID50438076 | Phenylboronate acrylamide | BL009552 | SY066256 | AKOS006291555 | AKOS003632579 | FT-0685348 | 3-Acrylamidophenylboronic acid

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

3-Acrylamidophenylboronic acid (AAPBA) is a monomeric compound of boronic acid. The boronic acid group (-B(OH)₂) can form reversible covalent bonds with certain molecules such as diols or sugars. This unique property can be used in the design of molecular sensors to detect and quantify specific types of analytes, such as sugars and biomolecules. The hydrophilicity of the amide group makes it more suitable for drug delivery applications. It can also be used as a synthetic building block to synthesize boronic acid polymers or copolymers for use in biomedical engineering and glucose monitoring biosensors.
Application
3-Acrylamidophenylboronic acid can be used:
As a monomer to synthesize methacrylic acid-3-acrylamidophenylboronic acid copolymer (PMAA-co-AAPBA), which is used as a supramolecular receptor for biosensors. AAPBA helps to enhance the water solubility and binding affinity of the copolymer. This copolymer is used for carbohydrate sensing in aqueous solution.
As a monomer to prepare poly (3-acrylamidophenylboronic acid-b-diethylene glycol dimethacrylate) to make glucose-sensitive nanoparticles for insulin delivery. The specific binding of AAPBA to the diol in the glucose molecule can induce glucose response to the block copolymer.
As a monomer and cross-linker to synthesize self-healing composite hydrogels for tissue engineering and drug delivery systems. This gel can mimic the properties of natural tissues and provide an environment suitable for cell growth. AAPBA polymerizes with acrylamide and acts on the (HPG) cis-diol group of hydroxypropyl guar guar to form a hydrogel with good mechanical strength and rapid self-healing properties.

Specifications

Synonyms

A846009 | AC-30997 | [3-(prop-2-enamido)phenyl]boronic acid | SCHEMBL235432 | 3-Acrylamidobenzeneboronic Acid | DTXSID50438076 | Phenylboronate acrylamide | BL009552 | SY066256 | AKOS006291555 | AKOS003632579 | FT-0685348 | 3-Acrylamidophenylboronic acid

Specifications & Purity

≥97%

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 504765393
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504765393
• Canonical Smiles: B(C1=CC(=CC=C1)NC(=O)C=C)(O)O
• IUPAC Name: [3-(prop-2-enoylamino)phenyl]boronic acid
• InChIKey: ULVXDHIJOKEBMW-UHFFFAOYSA-N
• 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)
• Isomeric SMILES: B(C1=CC(=CC=C1)NC(=O)C=C)(O)O
• Molecular Weight: 190.99
• Reaxy-Rn: 9908929
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=9908929&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Anilides

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Anilides
• Intermediate Tree Nodes: Not available
• Direct Parent: Anilides
• Alternative Parents: N-arylamides Acrylic acids and derivatives Secondary carboxylic acid amides Boronic acids Organic metalloid salts Organometalloid compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Anilide - N-arylamide - Acrylic acid or derivatives - Boronic acid derivative - Boronic acid - Carboxamide group - Secondary carboxylic acid amide - Carboxylic acid derivative - Organic metalloid salt - Organic nitrogen compound - Carbonyl group - Organooxygen compound - Organonitrogen compound - Organic metalloid moeity - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Melt Point(°C): 129-146°C
• Molecular Weight: 190.990 g/mol
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 191.075 Da
• Monoisotopic Mass: 191.075 Da
• Topological Polar Surface Area: 69.600 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 220.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

XLogP3

References

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