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Best Supplier 2,6-Dimethylphenylboronic acid丨CAS 100379-00-8
2,6-Dimethylphenylboronic acid (CAS 100379-00-8), also known as 2,6-dimethylbenzeneboronic acid, is an aromatic organoboron compound featuring a boronic acid group and two methyl substituents at the ortho-positions of a benzene ring. The two methyl groups create steric hindrance around the boronic acid functionality, influencing its reactivity and the properties of the resulting coupling products. This compound is a useful building block for pharmaceutical intermediate synthesis, sterically hindered biaryl compounds, medicinal chemistry, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C8H11BO2/c1-6-4-3-5-7(2)8(6)9(10)11/h3-5,10-11H,1-2H3 |
| InChI Key | ZXDTWWZIHJEZOG-UHFFFAOYSA-N |
| Smiles | CC1=C(B(O)O)C(C)=CC=C1 |
| EC No. | 600-084-4 |
| MDL No. | MFCD01009693 |
| PubChem CID | 583322 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
2,6-Dimethylphenylboronic acid serves as a coupling partner in Suzuki–Miyaura cross-coupling reactions for preparing ortho-substituted biaryl and aryl–heteroaryl compounds. Its two ortho-methyl groups introduce steric effects that can influence coupling efficiency and product conformation. Under appropriately optimized catalytic conditions, it can react with compatible organic halides to introduce a 2,6-dimethylphenyl fragment into complex aromatic structures.
Applications in Pharmaceutical Intermediate Synthesis
This compound is used as a building block for preparing sterically substituted aromatic intermediates in pharmaceutical research. Its boronic acid functionality enables carbon–carbon bond formation, while the two methyl groups provide a defined substitution pattern that can influence molecular shape, lipophilicity, and steric interactions. These characteristics support the preparation of structurally diverse intermediates for multistep synthesis.
Applications in Medicinal Chemistry
In medicinal chemistry, 2,6-Dimethylphenylboronic acid provides a route for incorporating a sterically hindered phenyl group into candidate molecules. Ortho-substitution can influence the orientation of adjacent aromatic rings and the conformational preferences of biaryl structures. Researchers may use this compound in analog synthesis, lead optimization, and structure–activity relationship studies to investigate the effects of steric and hydrophobic substitution.
Applications in Heterocyclic Compound Synthesis
The compound is particularly useful for constructing biaryl molecules containing a 2,6-dimethylphenyl unit. The two ortho-methyl groups can restrict rotation around the biaryl bond, affecting molecular conformation and potentially contributing to atropisomeric behavior in appropriately substituted structures. This makes it relevant to the synthesis and investigation of conformationally restricted aromatic compounds.
