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Top Rated 4-(Methanesulfonyl)phenylboronic acid丨CAS 149104-88-1
4-(Methanesulfonyl)phenylboronic acid (CAS 149104-88-1), also known as 4-(methylsulfonyl)phenylboronic acid, is a functionalized aromatic organoboron compound containing a boronic acid group and a methylsulfonyl substituent at the para-positions of a benzene ring. The boronic acid group provides synthetic versatility, while the strongly electron-withdrawing methylsulfonyl group influences the electronic properties and polarity of the aromatic structure. This combination makes the compound a useful building block for pharmaceutical intermediates, medicinal chemistry, agrochemical research, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C7H9BO4S/c1-13(11,12)7-4-2-6(3-5-7)8(9)10/h2-5,9-10H,1H3 |
| InChI Key | VDUKDQTYMWUSAC-UHFFFAOYSA-N |
| Smiles | C1=C([S](=O)(=O)C)C=CC(=C1)B(O)O |
| EC No. | 677-559-8 |
| MDL No. | MFCD01630820 |
| PubChem CID | 2734364 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
4-(Methanesulfonyl)phenylboronic acid can serve as an organoboron coupling partner in Suzuki–Miyaura reactions for preparing substituted biaryl and aryl–heteroaryl compounds. Under appropriately optimized 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 para-methylsulfonylphenyl fragment into complex molecular frameworks while retaining the sulfone functionality.
Applications in Medicinal Chemistry
In medicinal chemistry, 4-(Methanesulfonyl)phenylboronic acid provides a route for incorporating a methylsulfonyl-substituted aromatic fragment into candidate molecules. Sulfone groups are frequently investigated because they can influence molecular polarity, hydrogen-bond-accepting interactions, and physicochemical properties. Researchers may use this compound in analog synthesis, lead optimization, and structure–activity relationship studies to evaluate the effects of sulfone substitution.
Applications in Pharmaceutical Intermediate Synthesis
This compound is useful for preparing sulfone-containing aromatic intermediates in pharmaceutical research. The methylsulfonyl group provides a stable, polar functional group that can influence molecular properties, while the boronic acid functionality supports the construction of more complex aromatic structures. These characteristics make it suitable for developing substituted biaryl intermediates and other specialized pharmaceutical building blocks.
Applications in Functionalized Biaryl Synthesis
The compound is valuable for constructing biaryl structures containing a para-methylsulfonyl substituent. Its boronic acid group enables coupling with selected aromatic or heteroaromatic partners, allowing researchers to prepare molecular frameworks with defined substitution patterns. The resulting sulfone-containing compounds may be investigated for their electronic properties, molecular interactions, and suitability as advanced synthetic intermediates.
