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3,4-Dimethoxyphenylboronic acid (CAS 122775-35-3), also known as 3,4-dimethoxybenzeneboronic acid, is a functionalized aromatic organoboron compound containing a boronic acid group and two methoxy substituents at the 3- and 4-positions of a benzene ring. The electron-donating methoxy groups influence the electronic properties of the aromatic system, while the boronic acid functionality enables carbon–carbon bond formation. This compound is a useful building block for pharmaceutical intermediate synthesis, medicinal chemistry, natural product research, and specialty organic chemistry.
Chemical Identifiers
| InChI | 1S/C8H11BO4/c1-12-7-4-3-6(9(10)11)5-8(7)13-2/h3-5,10-11H,1-2H3 |
| InChI Key |
RCVDPBFUMYUKPB-UHFFFAOYSA-N |
| Smiles | OB(C1=CC=C(OC)C(OC)=C1)O |
| EC No. | 679-694-8 |
| MDL No. | MFCD01074574 |
| PubChem CID | 2734702 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
3,4-Dimethoxyphenylboronic acid is a useful coupling partner in Suzuki–Miyaura reactions for preparing methoxy-substituted biaryl and aryl–heteroaryl compounds. Under suitable palladium-catalyzed conditions, its boronic acid group reacts with compatible aromatic halides to form new carbon–carbon bonds. This transformation enables the introduction of a 3,4-dimethoxyphenyl fragment into complex molecular structures while retaining the methoxy substituents for subsequent synthetic modifications.
Applications in Pharmaceutical Intermediate Synthesis
This compound serves as a building block for preparing methoxy-substituted aromatic intermediates used in pharmaceutical research. Its boronic acid functionality supports the construction of complex aromatic frameworks, while the methoxy groups provide useful electronic and structural characteristics. These features make it relevant to multistep pharmaceutical intermediate synthesis and the preparation of structurally diverse research compounds.
Applications in Medicinal Chemistry
In medicinal chemistry, 3,4-Dimethoxyphenylboronic acid provides a convenient route for incorporating a dimethoxy-substituted phenyl group into candidate molecules. Methoxy groups can influence molecular polarity, hydrogen-bond-accepting interactions, and metabolic behavior. Researchers may use this compound in analog synthesis, lead optimization, and structure–activity relationship studies to investigate the effects of aromatic methoxy substitution.
Applications in Functionalized Biaryl Synthesis
The compound is valuable for constructing biaryl structures containing a defined 3,4-dimethoxyphenyl fragment. Its boronic acid group enables coupling with suitable aromatic partners, while the methoxy substituents influence electronic distribution and molecular interactions. These characteristics support the preparation of advanced aromatic intermediates and the investigation of molecular structure–property relationships.
