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Purchase Bulk 3-Nitrophenylboronic Acid丨CAS 13331-27-6
3-Nitrophenylboronic acid, CAS 13331-27-6, is a functionalized aromatic organoboron compound containing a boronic acid group and a nitro substituent at the meta position of a benzene ring. Its molecular structure combines the versatility of organoboron chemistry with the electron-withdrawing characteristics of the nitro group. The boronic acid functionality makes it a useful building block for palladium-catalyzed Suzuki–Miyaura cross-coupling reactions, enabling the formation of carbon–carbon bonds and the preparation of substituted aromatic compounds. Meanwhile, the nitro group provides an additional site for chemical transformation, including reduction to an amino group. These features make 3-Nitrophenylboronic acid valuable in pharmaceutical intermediate synthesis, heteroaromatic chemistry, and specialty chemical development.
Chemical Identifiers
| InChI | 1S/C6H6BNO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4,9-10H |
| InChI Key | ZNRGSYUVFVNSAW-UHFFFAOYSA-N |
| Smiles | C1=C(C=CC=C1[N+]([O-])=O)B(O)O |
| EC No. | 603-734-5 |
| MDL No. | MFCD00007193 |
| PubChem CID | 1677 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
3-Nitrophenylboronic acid is useful in medicinal chemistry and pharmaceutical research for introducing a meta-nitrophenyl unit into more complex molecular structures. Through Suzuki–Miyaura cross-coupling with suitable aryl or heteroaryl halides, it enables the preparation of diverse biaryl and heteroaryl compounds. The nitro group can subsequently be reduced to an amino group, providing access to aminated aromatic intermediates that can undergo further reactions such as acylation, sulfonylation, and alkylation. This combination of coupling and functional-group transformation supports the preparation of diversified intermediates for drug discovery and synthetic development.
Applications in Heterocyclic Compound Synthesis
The boronic acid group allows 3-Nitrophenylboronic acid to participate in cross-coupling reactions with compatible aromatic and heteroaromatic electrophiles. It provides a convenient route to introduce a 3-nitrophenyl group into larger molecular frameworks, producing substituted biaryl and heteroaryl structures. The meta-positioned nitro group gives the resulting compounds a defined substitution pattern and influences their electronic properties. These characteristics are useful in the preparation of molecular libraries, structural analogues, and functionalized aromatic intermediates.
Applications in Amino-Functionalized Compound Synthesis
An important synthetic application of 3-Nitrophenylboronic acid is its use as a precursor to amino-functionalized aromatic compounds. After the nitrophenyl group has been incorporated into a target structure, the nitro group can be reduced under suitable conditions to produce the corresponding amino derivative. The resulting amino group offers further opportunities for chemical modification, including the formation of amides, sulfonamides, and other nitrogen-containing structures. This approach provides flexibility for preparing complex aromatic compounds and pharmaceutical building blocks.
Applications in Specialty Chemicals and Functional Molecules
3-Nitrophenylboronic acid can support the synthesis of specialty organic molecules requiring electron-deficient aromatic structures. Its nitro substituent influences the electronic characteristics of the phenyl ring, while the boronic acid functionality enables molecular extension through suitable coupling reactions. Its derivatives may be explored in functional organic compounds, advanced aromatic materials, and research involving electronic effects and structure–property relationships. The ability to retain or transform the nitro group further expands the range of accessible molecular structures.
