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Bulk Supply 2-(Methylthio)benzeneboronic acid丨CAS 168618-42-6
2-(Methylthio)benzeneboronic acid (CAS 168618-42-6), also known as 2-(methylsulfanyl)phenylboronic acid, is an aromatic organoboron compound containing a boronic acid group and a methylthio substituent at adjacent positions on a benzene ring. Its structure combines the synthetic versatility of an arylboronic acid with the distinctive chemical properties of an organosulfur group. The boronic acid functionality enables carbon–carbon bond formation, while the methylthio group can influence electronic properties and undergo selected oxidation reactions. These characteristics make the compound a useful building block for medicinal chemistry, pharmaceutical intermediate development, sulfur-containing aromatic compounds, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C7H9BO2S/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5,9-10H,1H3 |
| InChI Key | QXBWTYBCNFKURT-UHFFFAOYSA-N |
| Smiles | OB(C1=CC=CC=C1SC)O |
| EC No. | 605-521-2 |
| MDL No. | MFCD01318165 |
| PubChem CID | 2773543 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
2-(Methylthio)benzeneboronic acid is useful in Suzuki–Miyaura cross-coupling reactions for preparing substituted biaryl and aryl–heteroaryl compounds. Under optimized palladium-catalyzed conditions, the boronic acid group can react with suitable aryl or heteroaryl halides to form new carbon–carbon bonds. This transformation enables the introduction of a 2-(methylthio)phenyl fragment into larger molecular structures. The ortho-methylthio group may influence coupling efficiency through steric effects and sulfur coordination to transition-metal catalysts, making reaction optimization important.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound serves as a building block for preparing sulfur-containing aromatic research molecules. Methylthio substituents can influence molecular lipophilicity, electronic distribution, and interactions with biological targets. Through suitable cross-coupling reactions, researchers can incorporate the methylthio-substituted phenyl fragment into structurally diverse candidate compounds. These derivatives may be investigated through lead optimization, analog synthesis, and structure–activity relationship studies.
Applications in Pharmaceutical Intermediate Synthesis
2-(Methylthio)benzeneboronic acid may support pharmaceutical intermediate synthesis requiring aromatic structures containing sulfur functionality. The boronic acid group provides a route for connecting the substituted phenyl fragment to suitable aromatic or heteroaromatic partners. The resulting methylthio-containing intermediates may undergo further transformations, including controlled oxidation to sulfoxide or sulfone derivatives. This approach enables researchers to prepare related compounds with different sulfur oxidation states and evaluate their chemical and biological properties.
Applications in Functionalized Biaryl Synthesis
2-(Methylthio)benzeneboronic acid is useful for constructing biaryl molecules containing an ortho-methylthio substituent. The boronic acid functionality enables coupling with compatible aromatic partners, producing substituted biphenyls and heterobiaryls. The sulfur-containing substituent may influence molecular conformation and intermolecular interactions. Its position adjacent to the newly formed aromatic linkage also provides opportunities to explore subsequent transformations and the synthesis of more complex sulfur-containing frameworks.
