Cas no 13506-83-7 (Boronic acid,1,2-phenylenebis- (9CI))

1,2-Phenylenebis(boronic acid) (9CI) is a bifunctional boronic acid derivative characterized by its two boronic acid groups attached to a benzene ring. This compound is widely utilized in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions, due to its ability to form stable boronate intermediates with aryl halides. Its rigid aromatic backbone enhances reactivity and selectivity in palladium-catalyzed transformations. The compound is also employed in the preparation of conjugated polymers, pharmaceuticals, and advanced materials. High purity grades ensure consistent performance in sensitive applications. Proper handling is recommended, as boronic acids may hydrolyze under prolonged exposure to moisture. Storage in a cool, dry environment is advised to maintain stability.
Boronic acid,1,2-phenylenebis- (9CI) structure
13506-83-7 structure
Product Name:Boronic acid,1,2-phenylenebis- (9CI)
CAS No:13506-83-7
MF:C6H8B2O4
MW:165.74732208252
CID:119671
PubChem ID:22174234
Update Time:2025-05-22

Boronic acid,1,2-phenylenebis- (9CI) Chemical and Physical Properties

Names and Identifiers

    • Boronic acid,1,2-phenylenebis- (9CI)
    • (2-boronophenyl)boronic acid
    • BORONIC ACID, 1,2-PHENYLENEBIS-BORONIC ACID
    • o-Benzenediboronic acid
    • 1,2-phenylenebisboronic acid
    • Boronic acid,1,2-phenylenebis-
    • benzenediboronic acid
    • MFCD28956996
    • 1,2-phenylenediboronic acid
    • Boronic acid, 1,2-phenylenebis- (9CI)
    • phenylenebisboronic acid
    • 1,2-Phenylenebis-boronic acid
    • 1,2-phenylenediboronicacid
    • CS-B1252
    • ZKRVXVDQQOVOIM-UHFFFAOYSA-N
    • SCHEMBL346128
    • Boronic acid, 1,2-phenylenebis-
    • DTXSID00623233
    • AMY1201
    • 13506-83-7
    • AKOS027397269
    • o-Benzenediboronicacid
    • A901695
    • D77287
    • DB-286146
    • SY279665
    • 2-(DIHYDROXYBORANYL)PHENYLBORONIC ACID
    • Inchi: 1S/C6H8B2O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4,9-12H
    • InChI Key: ZKRVXVDQQOVOIM-UHFFFAOYSA-N
    • SMILES: OB(C1C=CC=CC=1B(O)O)O

Computed Properties

  • Exact Mass: 164.06804
  • Monoisotopic Mass: 166.0608691g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 126
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 80.9?2

Experimental Properties

  • PSA: 80.92
  • LogP: -2.95380

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Boronic acid,1,2-phenylenebis- (9CI) Suppliers

Amadis Chemical Company Limited
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(CAS:13506-83-7)Boronic acid,1,2-phenylenebis- (9CI)
Order Number:A901695
Stock Status:in Stock
Quantity:1g/5g
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 12:09
Price ($):246.0/864.0

Additional information on Boronic acid,1,2-phenylenebis- (9CI)

Recent Advances in the Application of Boronic acid,1,2-phenylenebis- (9CI) (CAS: 13506-83-7) in Chemical Biology and Pharmaceutical Research

Boronic acid,1,2-phenylenebis- (9CI) (CAS: 13506-83-7), a bifunctional boronic acid derivative, has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound, characterized by its two boronic acid groups attached to a benzene ring, exhibits unique reactivity and binding properties, making it a valuable tool in drug discovery, sensor development, and materials science. Recent studies have explored its potential in targeted drug delivery, enzyme inhibition, and as a building block for functional materials, highlighting its broad utility in interdisciplinary research.

One of the most promising applications of Boronic acid,1,2-phenylenebis- (9CI) is in the development of protease inhibitors. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its efficacy as a reversible inhibitor of serine proteases, which are implicated in various pathological conditions, including cancer and inflammatory diseases. The study revealed that the compound's ability to form stable boronate esters with the active-site serine residue enhances its inhibitory potency, offering a novel mechanism for therapeutic intervention. This finding opens new avenues for the design of boronic acid-based inhibitors with improved selectivity and pharmacokinetic properties.

In addition to its therapeutic potential, Boronic acid,1,2-phenylenebis- (9CI) has been employed in the development of advanced biosensors. A recent ACS Sensors publication (2024) highlighted its use in glucose sensing, where the compound's boronic acid groups selectively bind to diols, enabling the detection of glucose at physiologically relevant concentrations. The study reported a significant improvement in sensor stability and response time compared to traditional boronic acid-based sensors, underscoring the compound's advantages in diagnostic applications. This innovation holds promise for continuous glucose monitoring systems, particularly for diabetes management.

Material science has also benefited from the unique properties of Boronic acid,1,2-phenylenebis- (9CI). Researchers have utilized its ability to form dynamic covalent bonds to create self-healing polymers and responsive hydrogels. A 2023 Advanced Materials study described the synthesis of a boronic acid-based hydrogel that exhibits pH-responsive swelling behavior, making it suitable for controlled drug release applications. The hydrogel's reversible cross-linking via boronate ester formation allows for tunable mechanical properties and degradation rates, addressing key challenges in biomaterial design. These advancements highlight the compound's versatility beyond traditional pharmaceutical applications.

Despite these promising developments, challenges remain in the optimization of Boronic acid,1,2-phenylenebis- (9CI) for clinical and industrial use. Issues such as solubility, stability in physiological conditions, and potential off-target effects require further investigation. Ongoing research aims to address these limitations through structural modifications and formulation strategies. For instance, a 2024 Chemical Communications report proposed the use of nanoparticle carriers to enhance the delivery and bioavailability of boronic acid-based therapeutics, demonstrating improved efficacy in preclinical models. Such innovations are critical for translating laboratory findings into practical applications.

In conclusion, Boronic acid,1,2-phenylenebis- (9CI) (CAS: 13506-83-7) represents a multifaceted compound with significant potential in chemical biology and pharmaceutical research. Its applications span from drug discovery to biosensing and materials engineering, driven by its unique chemical properties. As research continues to uncover new functionalities and optimize existing ones, this compound is poised to play an increasingly important role in addressing complex biomedical challenges. Future studies should focus on overcoming current limitations and exploring novel applications to fully realize its potential in the field.

Recommended suppliers
Amadis Chemical Company Limited
(CAS:13506-83-7)Boronic acid,1,2-phenylenebis- (9CI)
A901695
Purity:99%/99%
Quantity:1g/5g
Price ($):246.0/864.0
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