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High Purity (2-Nitrophenyl)boronic acid丨CAS 5570-19-4
(2-Nitrophenyl)boronic acid (CAS 5570-19-4), also known as 2-nitrobenzeneboronic acid, is an organoboron compound containing a boronic acid group and a nitro substituent at the ortho position of a benzene ring. Its combination of cross-coupling reactivity and a chemically versatile nitro group makes it a useful building block in organic synthesis. The boronic acid functionality enables carbon–carbon bond formation through Suzuki–Miyaura coupling, while the nitro group provides a potential site for further transformations, including reduction to an amino group. These features make it valuable in pharmaceutical intermediate synthesis, heterocyclic chemistry, and the preparation of functional aromatic compounds.
Chemical Identifiers
| InChI | 1S/C6H6BNO4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4,9-10H |
| InChI Key | SFUIGUOONHIVLG-UHFFFAOYSA-N |
| Smiles | O=[N+](C1=CC=CC=C1B(O)O)[O-] |
| EC No. | 611-304-3 |
| MDL No. | MFCD00161358 |
| PubChem CID | 2773548 |
Applications
Applications in Pharmaceutical and Agrochemical Intermediate Synthesis
(2-Nitrophenyl)boronic acid can be used to introduce a 2-nitrophenyl unit into complex molecular structures. Through Suzuki–Miyaura cross-coupling with suitable aryl or heteroaryl halides, it provides access to nitro-substituted biaryl and heterobiaryl compounds. The resulting nitro-containing structures can serve as intermediates for further chemical modification. In particular, reduction of the nitro group can generate an amino functionality, opening routes to compounds used in medicinal chemistry and pharmaceutical intermediate development. This combination of coupling and subsequent functional group conversion supports the preparation of diverse molecular frameworks for drug discovery and synthetic research.
Applications in Organic Synthesis and Cross-Coupling Reactions
A major application of (2-Nitrophenyl)boronic acid is palladium-catalyzed Suzuki–Miyaura coupling. Under suitable conditions, the 2-nitrophenyl group is transferred to an organic coupling partner, forming a new carbon–carbon bond. This reaction enables the synthesis of ortho-nitro-substituted biphenyls and other functional aromatic compounds. The nitro group can be retained during coupling and used in subsequent transformations, offering flexibility in multi-step synthetic planning. Its ortho position also introduces steric and electronic effects that may influence the structure and properties of the resulting molecules.
Applications in Heterocyclic Chemistry
The compound is useful for preparing nitrophenyl-substituted heteroaromatic structures through coupling with suitable halogenated heterocycles. These products can serve as intermediates in the synthesis of nitrogen-containing heterocycles and other functional molecules. The nitro group provides an additional transformation pathway, particularly through reduction to an amino group, which can support subsequent cyclization, derivatization, or heterocycle construction. This makes (2-Nitrophenyl)boronic acid a useful building block for exploring new molecular architectures in medicinal and synthetic chemistry.
Applications in Functional Materials Research
Nitro-substituted aromatic compounds are investigated in the development of functional organic molecules because their electron-withdrawing groups can influence molecular electronic properties. By coupling (2-Nitrophenyl)boronic acid with different aromatic partners, researchers can prepare structurally diverse compounds for evaluating electronic effects, molecular conformation, and structure–property relationships. Its potential for further conversion into amino-substituted derivatives also expands the range of structures accessible for functional material research.
