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4-Formylphenylboronic acid pinacol ester (CAS 128376-64-7), also known as 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde, is a multifunctional aromatic organoboron compound containing a pinacol boronate ester group and an aldehyde group at the para-positions of a benzene ring. Its dual functionality makes it a versatile building block for pharmaceutical intermediate synthesis, medicinal chemistry, heterocyclic compound preparation, and functional materials research.
Chemical Identifiers
| InChI | 1S/C13H17BO3/c1-12(2)13(3,4)17-14(16-12)11-7-5-10(9-15)6-8-11/h5-9H,1-4H3 |
| InChI Key | DMBMXJJGPXADPO-UHFFFAOYSA-N |
| Smiles | CC1(C)OB(OC1(C)C)C1=CC=C(C=O)C=C1 |
| EC No. | 675-003-9 |
| MDL No. | MFCD04972375 |
| PubChem CID | 2769536 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
4-Formylphenylboronic acid pinacol ester is a useful coupling partner in Suzuki–Miyaura reactions for preparing aldehyde-functionalized biaryl and aryl–heteroaryl compounds. Under suitable palladium-catalyzed conditions, its pinacol boronate ester group can participate in carbon–carbon bond formation with compatible aromatic halides. The aldehyde group may remain intact under optimized conditions, allowing subsequent chemical modification of the resulting aromatic structures.
Applications in Medicinal Chemistry
In medicinal chemistry, 4-Formylphenylboronic acid pinacol ester provides a convenient route for incorporating a para-formylphenyl fragment into research molecules. The aldehyde functionality can react with suitable amines to form imines or undergo reductive amination to produce substituted amines. Researchers may use these transformations in analog synthesis, lead optimization, and structure–activity relationship studies.
Applications in Pharmaceutical Intermediate Synthesis
This compound serves as a building block for preparing aromatic aldehyde intermediates used in pharmaceutical research. Its boronate ester functionality enables the construction of complex molecular frameworks, while the aldehyde group provides opportunities for further transformations, including reductive amination, oxidation, and reduction. These complementary reaction pathways support multistep pharmaceutical intermediate synthesis and molecular diversification.
Applications in Heterocyclic Compound Synthesis
The aldehyde group makes this compound relevant to heterocyclic synthesis. Through suitable condensation and cyclization reactions, aldehyde-containing intermediates can be converted into various nitrogen- and oxygen-containing heterocyclic structures. Combined with cross-coupling chemistry, these transformations provide access to complex molecular frameworks used in pharmaceutical and specialty organic research.
