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Bulk Supplier 3,5-Dimethylisoxazole-4-boronic acid丨CAS 16114-47-9
3,5-Dimethylisoxazole-4-boronic acid, CAS 16114-47-9, is a heteroaromatic organoboron compound featuring a boronic acid group at the 4-position of a 3,5-dimethyl-substituted isoxazole ring. Its molecular structure combines the synthetic versatility of boronic acid chemistry with the distinctive properties of an oxygen- and nitrogen-containing five-membered heterocycle. The boronic acid functionality provides a useful site for carbon–carbon bond formation, particularly through palladium-catalyzed Suzuki–Miyaura cross-coupling reactions with suitable organic electrophiles. This makes the compound a valuable building block for pharmaceutical research, heterocyclic synthesis, and the development of specialty organic molecules.
Chemical Identifiers
| InChI | 1S/C5H8BNO3/c1-3-5(6(8)9)4(2)10-7-3/h8-9H,1-2H3 |
| InChI Key | DIIFZCPZIRQDIJ-UHFFFAOYSA-N |
| Smiles | CC1=C(C(=NO1)C)B(O)O |
| EC No. | 672-304-7 |
| MDL No. | MFCD02677945 |
| PubChem CID | 2734346 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
3,5-Dimethylisoxazole-4-boronic acid is useful in medicinal chemistry for introducing a dimethylisoxazole unit into more complex molecular structures. Through Suzuki–Miyaura cross-coupling with compatible aryl or heteroaryl halides, it enables the formation of carbon–carbon bonds and the preparation of heteroaryl-containing intermediates. Isoxazole rings are frequently explored in pharmaceutical research because their heteroatom arrangement and substitution patterns offer opportunities to modify molecular properties and investigate biological activity. This compound supports the synthesis of diversified intermediates for drug discovery and pharmaceutical development.
Applications in Heterocyclic Compound Synthesis
The isoxazole ring is an important structural motif in heterocyclic chemistry, and its incorporation into larger molecular frameworks can be achieved through suitable cross-coupling reactions. The boronic acid group at the 4-position of 3,5-Dimethylisoxazole-4-boronic acid provides a defined reaction site for attaching aromatic and heteroaromatic groups. By selecting different coupling partners, researchers can prepare a range of substituted isoxazole derivatives with controlled structural features. These compounds can serve as intermediates for further functionalization and heterocyclic molecule development.
Applications in Biaryl and Heteroaryl Synthesis
This compound is a useful coupling partner for constructing molecules that combine isoxazole and aromatic or heteroaromatic units. Its boronic acid functionality can participate in Suzuki–Miyaura coupling with suitable organic halides, allowing the preparation of diverse heteroaryl–aryl structures. The two methyl groups on the isoxazole ring provide a defined substitution pattern and influence the steric and electronic characteristics of the resulting molecules. Such structural diversity is valuable in synthetic chemistry, molecular library preparation, and medicinal chemistry research.
Applications in Specialty Chemicals and Functional Molecules
3,5-Dimethylisoxazole-4-boronic acid can also support the development of specialty organic compounds requiring functionalized heteroaromatic structures. Its isoxazole ring provides a nitrogen- and oxygen-containing molecular framework, while the boronic acid group enables further molecular construction. Through coupling reactions and subsequent chemical modifications, researchers can incorporate this building block into customized molecular architectures for specialty chemical research and advanced synthesis.
