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Large Volume 3-Aminophenylboronic acid丨CAS 30418-59-8
3-Aminophenylboronic acid, CAS 30418-59-8, is a bifunctional aromatic organoboron compound containing an amino group at the 3-position and a boronic acid group on the benzene ring. The combination of these two functional groups makes it a versatile building block for organic synthesis, pharmaceutical intermediate development, and functional molecule research. Its boronic acid functionality enables carbon–carbon bond formation through suitable cross-coupling reactions, particularly Suzuki–Miyaura coupling, while the amino group provides an additional site for chemical modification. This complementary reactivity makes 3-Aminophenylboronic acid useful for preparing structurally diverse aromatic compounds and more complex molecular frameworks.
Chemical Identifiers
| InChI | 1S/C6H8BNO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4,9-10H,8H2 |
| InChI Key | JMZFEHDNIAQMNB-UHFFFAOYSA-N |
| Smiles | OB(C1=CC=CC(N)=C1)O |
| EC No. | 250-189-0 |
| MDL No. | MFCD00007755 |
| PubChem CID | 92269 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
3-Aminophenylboronic acid is a valuable building block in medicinal chemistry, where functionalized aromatic compounds are frequently required for the construction of pharmaceutical intermediates and research compounds. Its boronic acid group can participate in Suzuki–Miyaura cross-coupling with suitable aryl or heteroaryl halides, allowing the introduction of an aminophenyl unit into larger molecular structures. The amino group can subsequently undergo reactions such as acylation, sulfonylation, or reductive alkylation, depending on the target structure. These transformations provide flexibility in preparing diverse intermediates for drug discovery and synthetic development.
Applications in Heterocyclic Compound Synthesis
The amino group in 3-Aminophenylboronic acid offers opportunities for constructing nitrogen-containing heterocycles and functionalized aromatic derivatives. It can participate in condensation and other nitrogen-based reactions with suitable reagents, while the boronic acid group provides a separate route for carbon–carbon bond formation. By combining these reaction pathways, chemists can design multi-step synthetic routes for preparing complex heterocyclic and heteroaromatic compounds. This makes the compound relevant to heterocyclic chemistry, medicinal chemistry, and advanced intermediate synthesis.
Applications in Biaryl and Functional Aromatic Synthesis
Through Suzuki–Miyaura coupling, 3-Aminophenylboronic acid can introduce an amino-substituted phenyl group into a wide range of compatible aromatic and heteroaromatic structures. The resulting biaryl compounds can be further modified through reactions involving the amino group, enabling the preparation of molecules with different functional groups and substitution patterns. This versatility is useful in the development of molecular libraries, specialty aromatic intermediates, and compounds requiring multiple functionalization steps.
Applications in Functional Materials Research
Amino-functionalized aromatic compounds are useful building blocks in the development of specialty molecules and functional materials. 3-Aminophenylboronic acid provides a route to incorporate an aminophenyl unit into larger molecular architectures through cross-coupling chemistry. The amino group can serve as a site for introducing additional chemical linkages or functional groups, while the aromatic framework contributes rigidity and structural definition. Its derivatives may be investigated in functional organic molecules, polymer-related research, and advanced material development.
