Hangzhou Leap Chem Co., Ltd. is one of the most professional manufacturers and suppliers of (2-aminophenyl)boronic acid丨cas 5570-18-3 in China. Welcome to wholesale bulk high quality chemical products at competitive price from our factory. If you have any enquiry about custom service, please feel free to email us.
Good Quality (2-Aminophenyl)boronic acid丨CAS 5570-18-3
(2-Aminophenyl)boronic acid (CAS 5570-18-3), also known as 2-aminobenzeneboronic acid, is an organoboron compound featuring both a boronic acid group and an amino group at adjacent positions on a benzene ring. This combination of functional groups makes it a versatile building block for organic synthesis, particularly in the preparation of nitrogen-containing heterocycles and functional aromatic compounds. The boronic acid functionality enables carbon–carbon bond formation through Suzuki–Miyaura coupling, while the neighboring amino group provides additional opportunities for cyclization, derivatization, and other chemical transformations. Its multifunctional structure makes it useful in pharmaceutical research, heterocyclic chemistry, and advanced intermediate development.
Chemical Identifiers
| InChI | 1S/C6H8BNO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4,9-10H,8H2 |
| InChI Key | DIRRKLFMHQUJCM-UHFFFAOYSA-N |
| Smiles | NC1=CC=CC=C1B(O)O |
| EC No. | 611-303-8 |
| MDL No. | MFCD01074645 |
| PubChem CID | 2773216 |
Applications
Applications in Pharmaceutical and Agrochemical Intermediate Synthesis
(2-Aminophenyl)boronic acid is a useful intermediate for preparing aromatic compounds and heterocyclic structures relevant to medicinal chemistry. Its boronic acid group can participate in Suzuki–Miyaura cross-coupling with suitable aryl or heteroaryl halides, allowing the introduction of an amino-substituted phenyl unit into more complex molecular frameworks. The amino group offers an additional reaction site for acylation, alkylation, and other functional group transformations. These features support the synthesis of diverse intermediates for pharmaceutical research, lead optimization, and structure–activity relationship studies.
Applications in Heterocyclic Chemistry and Cyclization Reactions
The adjacent amino and boronic acid functionalities provide opportunities for developing synthetic routes to nitrogen-containing compounds. The amino group can participate in condensation and derivatization reactions, while the boronic acid group offers a route to further functionalization of the aromatic ring. Depending on the selected reaction partners and conditions, this combination can support the preparation of substituted heterocyclic intermediates and structurally diverse aromatic molecules. Such transformations are valuable in research involving benzimidazole-related structures, fused heterocycles, and other nitrogen-containing molecular frameworks. The specific synthetic pathway depends on the substrate design and reaction conditions.
Applications in Organic Synthesis and Cross-Coupling Reactions
A key application of (2-Aminophenyl)boronic acid is Suzuki–Miyaura cross-coupling with suitable organic halides. In the presence of an appropriate palladium catalyst and base, the aryl group can be transferred to an aromatic or heteroaromatic coupling partner, forming a new carbon–carbon bond. This provides access to amino-substituted biaryl and heterobiaryl compounds. The amino functionality can be retained for subsequent derivatization or incorporated into further synthetic steps. Because the amino group may coordinate with metal catalysts or influence reaction behavior, catalyst selection and reaction conditions should be optimized for individual substrates.
Applications in Chemical Biology and Functional Molecule Research
Amino-substituted aromatic structures are important components in the design of functional molecules and biologically relevant compounds. (2-Aminophenyl)boronic acid provides a route to combining an amino-bearing aromatic framework with boron-containing functionality. The amino group can be modified to adjust molecular properties, while the boronic acid group may offer opportunities for further molecular construction and investigation of boron-containing compounds. These characteristics make the compound relevant to exploratory research in chemical biology, medicinal chemistry, and functional molecule development.
