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Best Quality 3,5-Dimethylisoxazole-4-boronic acid pinacol ester丨CAS 832114-00-8
3,5-Dimethylisoxazole-4-boronic acid pinacol ester (CAS 832114-00-8) is a heteroaromatic organoboron compound featuring a 3,5-dimethylisoxazole ring with a pinacol boronate ester group at the 4-position. The isoxazole ring is a five-membered aromatic heterocycle containing adjacent nitrogen and oxygen atoms, while the two methyl substituents provide a defined substitution pattern. The pinacol boronate functionality makes this compound a useful building block for carbon–carbon bond-forming reactions, particularly in the synthesis of substituted heteroaromatic molecules. Its combination of heterocyclic structure, organoboron reactivity, and methyl substitution makes it relevant to medicinal chemistry, pharmaceutical intermediate development, agrochemical research, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C11H18BNO3/c1-7-9(8(2)14-13-7)12-15-10(3,4)11(5,6)16-12/h1-6H3 |
| InChI Key | CVLHETBAROWASE-UHFFFAOYSA-N |
| Smiles | B1(OC(C(O1)(C)C)(C)C)C2=C(ON=C2C)C |
| EC No. | 675-095-0 |
| MDL No. | MFCD05863910 |
| PubChem CID | 2758656 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
3,5-Dimethylisoxazole-4-boronic acid pinacol ester can be used in suitable Suzuki–Miyaura cross-coupling reactions to construct carbon–carbon bonds between heteroaromatic and aromatic fragments. Under appropriately optimized palladium-catalyzed conditions, the boronate ester functionality may react with compatible aryl or heteroaryl halides and pseudohalides to produce 4-substituted 3,5-dimethylisoxazole derivatives. This transformation enables the introduction of a defined isoxazole fragment into complex molecular frameworks. Reaction optimization may be necessary because heteroarylboron compounds can exhibit substrate-dependent stability and coupling efficiency.
Applications in Medicinal Chemistry
In medicinal chemistry, 3,5-Dimethylisoxazole-4-boronic acid pinacol ester serves as a building block for preparing isoxazole-containing research compounds and investigating structure–activity relationships. Isoxazole rings are widely explored in pharmaceutical discovery because their nitrogen and oxygen atoms contribute distinctive electronic characteristics and hydrogen-bond-accepting functionality. The two methyl substituents can influence molecular shape, hydrophobicity, and steric interactions. By using the boronate ester group for suitable coupling reactions, researchers can incorporate the 3,5-dimethylisoxazol-4-yl fragment into diverse molecular structures during lead optimization, analog synthesis, and compound library development.
Applications in Pharmaceutical Intermediate Synthesis
This compound may support pharmaceutical research programs requiring intermediates containing a substituted isoxazole ring. The boronate ester functionality provides a route for attaching the heteroaromatic fragment to selected aromatic or heteroaromatic coupling partners. The resulting products can serve as intermediates for further chemical modification or incorporation into more complex research molecules. Its defined substitution pattern is particularly useful when a 3,5-dimethylisoxazole unit is required in the target structure. These characteristics make the compound valuable for developing synthetic routes and preparing structurally diverse pharmaceutical research intermediates.
Applications in Agrochemical Research
Isoxazole-containing structures are investigated in agrochemical chemistry because heteroaromatic rings can contribute useful structural and electronic features to candidate molecules. 3,5-Dimethylisoxazole-4-boronic acid pinacol ester may serve as an intermediate for preparing research compounds containing a 3,5-dimethylisoxazole fragment. Through suitable cross-coupling reactions, this heterocyclic unit can be incorporated into larger molecular frameworks for evaluating physicochemical characteristics and potential biological activity. Its relevance to crop protection research depends on the design and properties of the resulting compounds.
