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3-Formylphenylboronic acid丨CAS 87199-16-4 Supplier in China
3-Formylphenylboronic acid (CAS 87199-16-4), also known as 3-formylbenzeneboronic acid or 3-boronobenzaldehyde, is a multifunctional aromatic organoboron compound containing a boronic acid group and an aldehyde group at the meta-positions of a benzene ring. Its structure combines the carbon–carbon bond-forming versatility of an arylboronic acid with the chemical reactivity of an aromatic aldehyde. These two functional groups provide complementary opportunities for molecular modification, making the compound a useful building block for medicinal chemistry, pharmaceutical intermediate development, heterocyclic synthesis, and functional organic materials research.
Chemical Identifiers
| InChI | 1S/C7H7BO3/c9-5-6-2-1-3-7(4-6)8(10)11/h1-5,10-11H |
| InChI Key | HJBGZJMKTOMQRR-UHFFFAOYSA-N |
| Smiles | C1=C(C=CC=C1C=O)B(O)O |
| EC No. | 628-589-5 |
| MDL No. | MFCD00161356 |
| PubChem CID | 2734356 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
3-Formylphenylboronic acid is useful in Suzuki–Miyaura cross-coupling reactions for preparing aldehyde-functionalized biaryl and aryl–heteroaryl compounds. Under optimized palladium-catalyzed conditions, the boronic acid group can react with compatible aryl or heteroaryl halides to form new carbon–carbon bonds. The aldehyde group may remain intact under suitable reaction conditions, allowing subsequent chemical modification. This approach provides an efficient route for introducing a meta-formylphenyl fragment into complex aromatic structures.
Applications in Medicinal Chemistry
In medicinal chemistry, 3-Formylphenylboronic acid serves as a building block for preparing structurally diverse aromatic research molecules. The aldehyde group offers a convenient site for introducing nitrogen-containing or other functional groups through selected chemical transformations. For example, reductive amination can convert suitable aldehyde-containing intermediates into substituted amines, while condensation reactions can generate imines and related derivatives. Combined with cross-coupling chemistry, these transformations support analog synthesis, molecular library development, and structure–activity relationship studies.
Applications in Pharmaceutical Intermediate Synthesis
3-Formylphenylboronic acid may support pharmaceutical intermediate synthesis requiring aromatic compounds with a reactive carbonyl group. The boronic acid functionality enables construction of substituted aromatic frameworks, while the aldehyde can undergo oxidation, reduction, or condensation reactions. Depending on the synthetic route, the aldehyde may be converted into a carboxylic acid, benzyl alcohol, or substituted amine. This flexibility allows chemists to prepare multiple intermediate structures from a common aromatic building block.
Applications in Heterocyclic Compound Synthesis
The aldehyde functionality makes this compound relevant to the preparation of nitrogen- and oxygen-containing heterocyclic structures. Aromatic aldehydes participate in condensation and cyclization reactions with suitable multifunctional reagents, providing routes to various heterocyclic frameworks. After Suzuki–Miyaura coupling, the resulting aldehyde-substituted aromatic intermediates may be used to construct imidazole, benzimidazole, or other heterocyclic derivatives under appropriately selected conditions. These transformations are useful in pharmaceutical research and specialty organic synthesis.
