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Purchase Bulk 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole丨CAS 761446-44-0
1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (CAS 761446-44-0) is a heteroaromatic boronic acid pinacol ester featuring a methyl group on the nitrogen atom at the 1-position and a pinacol boronate group at the 4-position of the pyrazole ring. This compound combines the structural characteristics of an N-methylpyrazole heterocycle with the synthetic versatility of an organoboron functional group. It is a useful building block for medicinal chemistry, pharmaceutical intermediate synthesis, heterocyclic chemistry, and specialty organic synthesis. The boronic ester functionality enables the introduction of a 1-methylpyrazol-4-yl fragment into more complex molecular structures through suitable carbon–carbon bond-forming reactions.
Chemical Identifiers
| InChI | InChI=1S/C10H17BN2O2/c1-9(2)10(3,4)15-11(14-9)8-6-12-13(5)7-8/h6-7H,1-5H3 |
| InChI Key | UCNGGGYMLHAMJG-UHFFFAOYSA-N |
| Smiles | B1(OC(C(O1)(C)C)(C)C)C2=CN(N=C2)C |
| EC No. | 616-293-9 |
| MDL No. | MFCD03789259 |
| PubChem CID | 2773987 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole is particularly useful in Suzuki–Miyaura cross-coupling reactions for preparing substituted pyrazole derivatives. Under appropriately selected palladium-catalyzed conditions, the pinacol boronate group can react with compatible aryl or heteroaryl halides and pseudohalides to form new carbon–carbon bonds. This reaction provides a practical route for incorporating the 1-methylpyrazol-4-yl unit into aromatic and heteroaromatic frameworks. The nitrogen-containing pyrazole ring may influence catalytic behavior, so reaction conditions should be optimized according to the coupling partner and target structure.
Applications in Medicinal Chemistry
In medicinal chemistry, this compound serves as a building block for synthesizing pyrazole-containing research compounds and investigating structure–activity relationships. Pyrazole rings are widely explored in pharmaceutical discovery because their nitrogen-containing aromatic structures can contribute to molecular recognition and influence physicochemical properties. The N-methyl substituent provides a defined substitution pattern, while the boronic ester group enables efficient incorporation of the heterocyclic fragment into suitable candidate molecules. Researchers may use this compound in lead optimization, analog preparation, and molecular library development.
Applications in Pharmaceutical Intermediate Synthesis
This compound may support pharmaceutical research programs requiring intermediates containing a 1-methylpyrazol-4-yl structural unit. Its boronic ester functionality provides a convenient synthetic route for constructing carbon–carbon bonds between the pyrazole ring and other molecular fragments. This capability is valuable in multistep synthesis strategies involving complex heteroaromatic structures. Depending on the target compound, the resulting intermediates may undergo further chemical transformations to produce specialized research molecules.
Applications in Specialty Organic Synthesis
Beyond pharmaceutical research, this compound can be used in specialty organic synthesis requiring a functionalized pyrazole building block. The pinacol boronate group provides a convenient organoboron functionality for selected synthetic transformations, while the N-methylpyrazole ring contributes a structurally defined heteroaromatic unit. It may support the preparation of advanced organic intermediates, functional molecules, and complex heterocyclic compounds, depending on the selected synthetic pathway and reaction compatibility.
