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Bulk Supplier 3-Tolylboronic acid丨CAS 17933-03-8
3-Tolylboronic acid, CAS 17933-03-8, also known as 3-methylphenylboronic acid or m-tolylboronic acid, is an aromatic organoboron compound featuring a boronic acid group and a methyl substituent at the meta position of a benzene ring. Its structure combines the versatility of boronic acid chemistry with the hydrophobic and electronic characteristics of a methyl-substituted aromatic ring. The boronic acid functionality makes it a useful building block for palladium-catalyzed Suzuki–Miyaura cross-coupling reactions, enabling the formation of carbon–carbon bonds and access to diverse substituted aromatic compounds. It is widely relevant to pharmaceutical intermediate synthesis, specialty chemical development, and functional organic molecule research.
Chemical Identifiers
| InChI | 1S/C7H9BO2/c1-6-3-2-4-7(5-6)8(9)10/h2-5,9-10H,1H3 |
| InChI Key | BJQCPCFFYBKRLM-UHFFFAOYSA-N |
| Smiles | CC1=CC(B(O)O)=CC=C1 |
| EC No. | 605-855-9 |
| MDL No. | MFCD00040198 |
| PubChem CID | 2733950 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
3-Tolylboronic acid is a useful building block in medicinal chemistry and pharmaceutical research, particularly for introducing a 3-methylphenyl group into more complex molecular structures. Through Suzuki–Miyaura cross-coupling with suitable aryl or heteroaryl halides, it enables the preparation of substituted biaryl compounds and other aromatic intermediates. The methyl substituent provides a defined structural feature that can influence molecular shape, hydrophobicity, and steric properties. This makes the compound valuable for exploring structural variations during drug discovery and preparing intermediates for pharmaceutical development.
Applications in Biaryl and Heteroaryl Synthesis
The boronic acid group in 3-Tolylboronic acid can react with compatible aromatic and heteroaromatic electrophiles under suitable cross-coupling conditions. This provides an efficient approach to introducing a meta-methyl-substituted phenyl unit into larger molecular frameworks. The resulting biaryl and heteroaryl compounds can serve as intermediates for additional functionalization or as components of molecular libraries. Its defined substitution pattern is especially useful when researchers need to control the position of substituents in aromatic structures.
Applications in Specialty Chemical Development
3-Tolylboronic acid can support the synthesis of specialty organic compounds that require methyl-substituted aromatic structures. The methyl group can influence the physical and chemical properties of the resulting molecules, while the boronic acid functionality provides a convenient route for carbon–carbon bond formation. This combination makes the compound suitable for preparing customized aromatic intermediates and structurally diverse derivatives for industrial research and specialty chemical development.
Applications in Functional Organic Materials
Methyl-substituted aromatic units are frequently incorporated into the design of functional organic molecules and advanced material precursors. Through cross-coupling reactions, 3-Tolylboronic acid can be used to introduce a 3-tolyl group into larger conjugated or aromatic frameworks. The resulting compounds may be investigated in organic electronic materials, optical materials, and other functional molecular systems. Its defined substitution pattern offers flexibility for studying how methyl groups affect molecular structure and material properties.
