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4-Nitrophenylboronic acid, CAS 24067-17-2, is a functionalized aromatic organoboron compound featuring a boronic acid group and a nitro group in the para positions of a benzene ring. Its molecular structure combines the versatility of boronic acid chemistry with the distinctive electronic properties of the electron-withdrawing nitro substituent. The boronic acid group provides a useful reaction site for palladium-catalyzed Suzuki–Miyaura cross-coupling, while the nitro group can undergo further transformations, including reduction to an amino group. This combination makes 4-Nitrophenylboronic acid a valuable building block for pharmaceutical intermediates, substituted aromatic compounds, and specialty chemical synthesis.
Chemical Identifiers
| InChI | 1S/C6H6BNO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4,9-10H |
| InChI Key | NSFJAFZHYOAMHL-UHFFFAOYSA-N |
| Smiles | OB(C1=CC=C([N+]([O-])=O)C=C1)O |
| EC No. | 627-647-7 |
| MDL No. | MFCD00161360 |
| PubChem CID | 2773552 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
4-Nitrophenylboronic acid is useful in medicinal chemistry and pharmaceutical intermediate development, particularly when a nitrophenyl unit is required in a target molecular structure. Through Suzuki–Miyaura cross-coupling with suitable aryl or heteroaryl halides, it enables the formation of carbon–carbon bonds and the preparation of substituted biaryl compounds. The nitro group provides an additional functional handle that can be reduced to an amino group under appropriate conditions, allowing further derivatization through acylation, sulfonylation, or other nitrogen-based reactions. These transformations support the preparation of diverse intermediates for drug discovery and synthetic research.
Applications in Biaryl and Heteroaryl Synthesis
The boronic acid functionality makes this compound suitable for cross-coupling with compatible aromatic and heteroaromatic electrophiles. It can introduce a 4-nitrophenyl group into larger molecular frameworks, providing access to a range of substituted biaryl and heteroaryl derivatives. The para-nitro substituent influences the electronic character of the aromatic ring and can be retained or modified in subsequent synthetic steps. This versatility is valuable for constructing molecular libraries, developing new aromatic scaffolds, and preparing intermediates for further functionalization.
Applications in Amino-Functionalized Compound Synthesis
One important synthetic application of 4-Nitrophenylboronic acid is its use in preparing amino-substituted aromatic compounds. After the nitrophenyl group has been introduced into a target structure through cross-coupling, the nitro group can be reduced to an amino group using a suitable reduction system. The resulting amino-functionalized compounds can undergo additional transformations to form amides, sulfonamides, imines, and other derivatives. This two-stage approach provides a practical route to diverse nitrogen-containing aromatic structures for pharmaceutical and specialty chemical research.
Applications in Functional Materials Research
The combination of a reactive boronic acid group and an electron-withdrawing nitro substituent makes this compound relevant to the development of functional organic molecules. Its coupling products may be investigated in research involving electronic effects, molecular conjugation, and structure–property relationships. The nitro group can also serve as a precursor to other nitrogen-containing functionalities, expanding the range of compounds accessible from the initial aromatic building block. These characteristics support research in specialty chemicals and advanced organic materials.
