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Top 1H-Pyrazole-4-boronic acid丨CAS 763120-58-7
1H-Pyrazole-4-boronic acid (CAS 763120-58-7) is a nitrogen-containing heteroaromatic boronic acid featuring a boronic acid group at the 4-position of a pyrazole ring. Its structure combines the chemical versatility of an organoboron functionality with the distinctive properties of a five-membered aromatic heterocycle containing two adjacent nitrogen atoms. This compound is a useful building block for medicinal chemistry, pharmaceutical intermediate development, heterocyclic synthesis, and specialty organic research. The boronic acid group enables carbon–carbon bond formation through suitable cross-coupling reactions, while the pyrazole ring provides opportunities for further functionalization and molecular diversification.
Chemical Identifiers
| InChI |
InChI=1S/C3H5BN2O2/c7-4(8)3-1-5-6-2-3/h1-2,7-8H,(H,5,6) |
| InChI Key | KEZNMOUMHOZFRA-UHFFFAOYSA-N |
| Smiles | B(C1=CNN=C1)(O)O |
| EC No. | 624-632-7 |
| MDL No. | MFCD07368251 |
| PubChem CID | 17750278 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
1H-Pyrazole-4-boronic acid can be used in Suzuki–Miyaura cross-coupling reactions to prepare substituted pyrazole derivatives and other heteroaryl-containing compounds. Under appropriately selected palladium-catalyzed conditions, the boronic acid functionality may react with compatible aryl or heteroaryl halides and pseudohalides to form new carbon–carbon bonds. This approach enables the introduction of a pyrazol-4-yl fragment into more complex molecular frameworks. Because the compound contains an unprotected pyrazole nitrogen system, reaction optimization may be necessary to address catalyst interactions, substrate stability, and competing reactions.
Applications in Medicinal Chemistry
In medicinal chemistry, 1H-Pyrazole-4-boronic acid serves as a building block for synthesizing pyrazole-containing research compounds and exploring structure–activity relationships. Pyrazole rings are widely investigated in pharmaceutical discovery because their nitrogen atoms can contribute to hydrogen-bonding interactions and influence molecular polarity and recognition. The boronic acid group provides a synthetic route for incorporating the pyrazole fragment into structurally diverse candidate molecules. Researchers may use this compound in lead optimization, analog synthesis, and molecular library development.
Applications in Pharmaceutical Intermediate Synthesis
This compound may support pharmaceutical research programs requiring intermediates containing a pyrazole structural unit. Its boronic acid functionality enables the construction of carbon–carbon bonds with suitable aromatic or heteroaromatic coupling partners. The resulting compounds can be further modified through appropriately designed synthetic transformations, including reactions involving the pyrazole nitrogen atoms when compatible conditions are selected. These characteristics make 1H-Pyrazole-4-boronic acid useful for preparing structurally defined pharmaceutical research intermediates and exploring alternative synthetic routes.
Applications in Heterocyclic Chemistry
1H-Pyrazole-4-boronic acid is particularly relevant to heterocyclic chemistry because it combines a reactive boronic acid group with an unsubstituted pyrazole nitrogen framework. The compound may be used to prepare substituted pyrazoles and other nitrogen-containing heteroaromatic molecules through selected coupling and functionalization reactions. Researchers can investigate the effects of substitution at the 4-position and explore subsequent modifications of the pyrazole ring. Its structural features make it useful for developing heterocyclic compound libraries and studying structure–property relationships.
