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Premium Chemicals 4-Formylphenylboronic Acid丨CAS 87199-17-5
4-Formylphenylboronic acid (CAS 87199-17-5), also known as 4-formylbenzeneboronic acid or 4-boronobenzaldehyde, is a multifunctional aromatic organoboron compound containing a boronic acid group and an aldehyde group at opposite, para-positions of a benzene ring. Its structure combines the carbon–carbon bond-forming utility of an arylboronic acid with the chemical reactivity of an aromatic aldehyde. These complementary functional groups make the compound a useful building block for medicinal chemistry, pharmaceutical intermediate synthesis, functionalized biaryl preparation, molecular recognition, and advanced materials research.
Chemical Identifiers
| InChI | 1S/C7H7BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5,10-11H |
| InChI Key | VXWBQOJISHAKKM-UHFFFAOYSA-N |
| Smiles | OB(C1=CC=C(C=O)C=C1)O |
| EC No. | 438-670-5 |
| MDL No. | MFCD00151823 |
| PubChem CID | 591073 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
4-Formylphenylboronic acid is useful in Suzuki–Miyaura cross-coupling reactions for preparing aldehyde-functionalized biaryl and aryl–heteroaryl compounds. Under appropriately optimized palladium-catalyzed conditions, the boronic acid group can react with compatible aryl or heteroaryl halides to form carbon–carbon bonds. The aldehyde group may remain intact under suitable reaction conditions, enabling subsequent chemical modification. Its para-substitution pattern provides a convenient route for constructing aromatic structures with functional groups positioned at opposite ends of the phenyl ring.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound serves as a building block for preparing structurally diverse aromatic research molecules. The aldehyde functionality enables transformations such as reductive amination, imine formation, and selected condensation reactions. These reactions allow researchers to introduce nitrogen-containing substituents and other molecular features after constructing the desired aromatic framework. Combined with cross-coupling chemistry, this approach supports lead optimization, analog synthesis, and structure–activity relationship studies.
Applications in Pharmaceutical Intermediate Synthesis
4-Formylphenylboronic acid may support pharmaceutical intermediate synthesis requiring aromatic structures containing a reactive aldehyde group. The boronic acid functionality provides a route for connecting the substituted phenyl fragment to suitable aromatic or heteroaromatic partners. The aldehyde can subsequently undergo oxidation to a carboxylic acid, reduction to a benzyl alcohol, or conversion into an amine-containing derivative through appropriate reactions. These transformations enable the preparation of multiple pharmaceutical research intermediates from a common building block.
Applications in Heterocyclic Compound Synthesis
The aldehyde group makes 4-Formylphenylboronic acid relevant to heterocyclic synthesis. Aromatic aldehydes can participate in condensation and cyclization reactions with suitable nitrogen- or oxygen-containing reagents. Following cross-coupling, the resulting aldehyde-functionalized aromatic intermediates may be used to construct substituted imidazoles, benzimidazoles, and other heterocyclic frameworks, depending on the selected reaction partners. These synthetic strategies are useful for preparing complex molecules in pharmaceutical and specialty chemical research.
