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High Quality Cyclopropylboronic acid丨CAS 411235-57-9
Cyclopropylboronic acid (CAS 411235-57-9) is an organoboron compound featuring a boronic acid group directly attached to a three-membered cyclopropyl ring. Unlike aromatic boronic acids, this compound contains an aliphatic carbon–boron bond and provides a useful route for introducing a cyclopropyl fragment into organic molecules. The cyclopropyl group is an important structural motif in medicinal chemistry because of its compact size, distinctive ring geometry, and influence on molecular conformation and physicochemical properties. By combining this strained cyclic framework with a reactive boronic acid functionality, Cyclopropylboronic acid serves as a valuable building block for pharmaceutical intermediate synthesis, medicinal chemistry, transition-metal-catalyzed coupling reactions, agrochemical research, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C3H7BO2/c5-4(6)3-1-2-3/h3,5-6H,1-2H2 |
| InChI Key | WLVKDFJTYKELLQ-UHFFFAOYSA-N |
| Smiles | OB(C1CC1)O |
| EC No. | 609-890-0 |
| MDL No. | MFCD04038750 |
| PubChem CID | 2760897 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
Cyclopropylboronic acid can be used in suitable Suzuki–Miyaura cross-coupling reactions to construct carbon–carbon bonds between cyclopropyl groups and aromatic or heteroaromatic fragments. Under appropriately optimized palladium-catalyzed conditions, the compound may react with compatible aryl or heteroaryl halides and pseudohalides to produce cyclopropyl-substituted organic molecules. This transformation provides a useful alternative to synthetic approaches involving prefunctionalized cyclopropyl halides. Because alkylboronic acids exhibit different reactivity from arylboronic acids, careful selection of catalysts, ligands, bases, and reaction conditions may be necessary to achieve efficient coupling while minimizing competing reactions.
Applications in Medicinal Chemistry
In medicinal chemistry, Cyclopropylboronic acid is a useful building block for preparing cyclopropyl-containing research compounds and investigating structure–activity relationships. Cyclopropyl groups are frequently incorporated into pharmaceutical candidate molecules because they provide a compact, conformationally restricted structural unit that can influence molecular shape, lipophilicity, and interactions with biological targets. Depending on the surrounding molecular framework, cyclopropyl substitution may also affect metabolic behavior and physicochemical characteristics. Researchers may use Cyclopropylboronic acid to introduce this fragment into suitable aromatic and heteroaromatic compounds during lead optimization, analog synthesis, and molecular library development.
Applications in Pharmaceutical Intermediate Synthesis
Cyclopropylboronic acid may support pharmaceutical research programs requiring intermediates containing a cyclopropyl structural unit. Its boronic acid functionality provides a route for connecting the cyclopropyl group to compatible coupling partners through selected carbon–carbon bond-forming reactions. The resulting compounds may serve as intermediates for further chemical modification or incorporation into more complex research molecules. The small ring size and distinctive geometry of the cyclopropyl fragment make it useful for exploring molecular modifications that influence steric interactions and conformational preferences. These characteristics support the development of synthetic routes to structurally diverse pharmaceutical intermediates.
Applications in Cyclopropyl-Substituted Heterocyclic Synthesis
Cyclopropylboronic acid is particularly relevant to the preparation of cyclopropyl-substituted heterocyclic compounds. Through suitable cross-coupling reactions, the cyclopropyl group may be introduced into nitrogen-, oxygen-, or sulfur-containing aromatic heterocycles. Such structures are of interest in medicinal chemistry and specialty chemical research because the combination of a heterocyclic ring and a compact cyclopropyl substituent provides distinctive molecular characteristics. Researchers may use this compound to prepare cyclopropyl-substituted pyridines, pyrazines, and other compatible heteroaromatic derivatives for further investigation.
