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Major Supplier 1,4-Benzenediboronic acid丨CAS 4612-26-4
1,4-Benzenediboronic acid (CAS 4612-26-4), also known as benzene-1,4-diboronic acid or para-phenylenediboronic acid, is an aromatic organoboron compound containing two boronic acid groups attached to opposite positions of a benzene ring. Its symmetrical molecular structure and dual boronic acid functionalities make it a valuable building block in organic synthesis, materials chemistry, and polymer research. Both boronic acid groups can participate in suitable chemical transformations, providing opportunities for constructing extended molecular structures, linking aromatic units, and preparing functional boron-containing materials.
Chemical Identifiers
| InChI | 1S/C6H8B2O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4,9-12H |
| InChI Key | BODYVHJTUHHINQ-UHFFFAOYSA-N |
| Smiles | C1=CC(=CC=C1B(O)O)B(O)O |
| EC No. | 628-888-0 |
| MDL No. | MFCD00236018 |
| PubChem CID | 230478 |
Applications
Applications in Organic Synthesis and Cross-Coupling Reactions
A key application of 1,4-Benzenediboronic acid is palladium-catalyzed Suzuki–Miyaura cross-coupling. Its two boronic acid groups provide two potential coupling sites, allowing sequential or double coupling with suitable aryl or heteroaryl halides. This enables the synthesis of extended biaryl structures, symmetrical aromatic compounds, and more complex conjugated molecules. The para-substituted benzene core provides a relatively linear molecular framework, which is useful when designing compounds with defined connectivity and extended aromatic systems. Reaction selectivity and the extent of coupling depend on the electrophilic partner, catalyst system, and reaction conditions.
Applications in Polymer Synthesis and Materials Chemistry
The bifunctional structure of 1,4-Benzenediboronic acid makes it relevant to the development of boron-containing polymers and covalent organic frameworks. Its two boronic acid groups can participate in condensation reactions with suitable diols or polyols to form boronate ester linkages. These reversible covalent bonds are useful in constructing porous and ordered materials, including boronate ester-linked covalent organic frameworks (COFs). Such materials are investigated for applications in gas adsorption, molecular separation, sensing, catalysis, and functional porous structures. Its aromatic core can contribute rigidity and structural regularity to the resulting material networks.
Applications in Pharmaceutical and Fine Chemical Research
1,4-Benzenediboronic acid can serve as a synthetic building block for preparing symmetrical or extended aromatic intermediates. Through controlled cross-coupling reactions, it enables the introduction of multiple aromatic or heteroaromatic substituents into a central benzene framework. This approach can support medicinal chemistry research, compound library preparation, and the development of specialized fine chemicals. Although it is not itself a pharmaceutical active ingredient, its bifunctional reactivity makes it useful in the synthesis of more complex molecular structures.
Applications in Chemical Sensors and Functional Materials
Boronic acid groups can interact reversibly with compounds containing suitable diol functionalities, forming boronate complexes under appropriate conditions. This property has attracted interest in molecular recognition, chemical sensing, and responsive material design. With two boronic acid groups positioned on a rigid aromatic core, 1,4-Benzenediboronic acid offers a platform for investigating multivalent interactions and incorporating boron-based recognition sites into functional molecular architectures.
