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Purchase Bulk 2-Formylphenylboronic acid丨CAS 40138-16-7
2-Formylphenylboronic acid, CAS 40138-16-7, is a bifunctional aromatic organoboron compound containing both a boronic acid group and an aldehyde group on adjacent positions of a benzene ring. The combination of these two reactive functionalities makes it a valuable building block for advanced organic synthesis. The boronic acid group supports carbon–carbon bond formation through Suzuki–Miyaura cross-coupling, while the formyl group provides a versatile site for condensation, oxidation, reduction, and other carbonyl-based transformations. Its multifunctional structure offers considerable flexibility in the preparation of pharmaceutical intermediates, heterocyclic compounds, and specialty organic molecules.
Chemical Identifiers
| InChI | 1S/C7H7BO3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5,10-11H |
| InChI Key | DGUWACLYDSWXRZ-UHFFFAOYSA-N |
| Smiles | O=CC1=CC=CC=C1B(O)O |
| EC No. | 628-526-1 |
| MDL No. | MFCD00151822 |
| PubChem CID | 292189 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
2-Formylphenylboronic acid is useful in medicinal chemistry and pharmaceutical intermediate development, where functionalized aromatic building blocks are required to construct complex molecular frameworks. Its boronic acid group can participate in palladium-catalyzed cross-coupling reactions with suitable aryl or heteroaryl halides, introducing a substituted aromatic unit into target molecules. Meanwhile, the aldehyde group provides opportunities for further structural modification, including reductive amination and condensation reactions. This combination supports the preparation of diversified intermediates for drug discovery and synthetic research.
Applications in Biaryl and Heteroaryl Synthesis
The neighboring boronic acid and aldehyde functionalities make this compound particularly interesting for the construction of more complex molecular structures. The aldehyde group can participate in reactions with suitable nitrogen- or oxygen-containing reagents to form imines and other functionalized products, while the boronic acid group enables additional coupling chemistry. Depending on the reaction design, these complementary functional groups can be used in sequential synthetic transformations to access substituted aromatic and heterocyclic compounds. Such applications are valuable in heterocyclic chemistry and the development of specialized research intermediates.
Applications in Functional Organic Materials
The aldehyde group in 2-Formylphenylboronic acid offers a convenient route to multiple derivatives. It can be converted into alcohols, carboxylic acids, imines, and other functional groups through appropriate chemical transformations. The boronic acid functionality provides another reaction site for carbon–carbon bond construction and the preparation of organoboron-derived compounds. This dual functionality allows chemists to explore different reaction sequences and develop synthetic routes in which the aromatic framework can be modified at more than one position.
Applications in Specialty Chemical Development
Functionalized aromatic compounds are important building blocks in the development of specialty chemicals and advanced organic materials. 2-Formylphenylboronic acid can be incorporated into larger molecular structures through cross-coupling and carbonyl chemistry. The aldehyde group may be used to introduce linkers or additional functional units, while the boronic acid group enables the extension of aromatic frameworks. These characteristics make the compound relevant to research involving functional molecules, customized aromatic intermediates, and the synthesis of structurally diverse materials.
