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Purchasing Bulk 2-Cyanophenylboronic acid丨CAS 138642-62-3
2-Cyanophenylboronic acid (CAS 138642-62-3), also known as 2-cyanobenzeneboronic acid or 2-boronobenzonitrile, is a functionalized aromatic organoboron compound containing a boronic acid group and a cyano group at adjacent positions of a benzene ring. The electron-withdrawing nitrile functionality influences the electronic properties of the aromatic structure, while the boronic acid group provides a useful site for carbon–carbon bond formation. This compound is a versatile building block for pharmaceutical intermediates, medicinal chemistry, heterocyclic synthesis, and specialty organic research.
Chemical Identifiers
| InChI | 1S/C7H6BNO2/c9-5-6-3-1-2-4-7(6)8(10)11/h1-4,10-11H |
| InChI Key | NPLZNDDFVCGRAG-UHFFFAOYSA-N |
| Smiles | OB(C1=CC=CC=C1C#N)O |
| EC No. | 604-090-8 |
| MDL No. | MFCD01632208 |
| PubChem CID | 2734610 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
2-Cyanophenylboronic acid can be used as an organoboron coupling partner in Suzuki–Miyaura reactions to prepare nitrile-substituted biaryl and aryl–heteroaryl compounds. Under appropriately optimized palladium-catalyzed conditions, its boronic acid group reacts with compatible aromatic halides to form new carbon–carbon bonds. The cyano group can remain intact under suitable conditions, allowing further modification of the resulting aromatic intermediates.
Applications in Medicinal Chemistry
In medicinal chemistry, 2-Cyanophenylboronic acid provides a convenient route for introducing an ortho-cyanophenyl fragment into research molecules. Nitrile groups are frequently investigated because they can influence molecular polarity, electronic distribution, and interactions with biological targets. Researchers may use this compound in analog synthesis, lead optimization, and structure–activity relationship studies to evaluate the effects of nitrile substitution.
Applications in Pharmaceutical Intermediate Synthesis
This compound is useful for preparing nitrile-containing aromatic intermediates in pharmaceutical research. Its boronic acid functionality enables the construction of complex molecular frameworks, while the cyano group provides an additional site for chemical transformation. Under suitable reaction conditions, nitrile groups can be converted into amides, carboxylic acids, amines, or selected heterocyclic derivatives, supporting multistep pharmaceutical intermediate synthesis.
Applications in Heterocyclic Compound Synthesis
The nitrile functionality makes 2-Cyanophenylboronic acid relevant to heterocyclic synthesis. Following suitable cross-coupling reactions, the resulting nitrile-containing intermediates may undergo cyclization or functional group transformations to produce nitrogen-containing heterocycles. For example, nitrile groups can serve as precursors for tetrazole formation under appropriate conditions. These transformations support the preparation of structurally diverse heterocyclic building blocks.
