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Large Volume (Naphthalen-2-yl)boronic acid丨CAS 32316-92-0
(Naphthalen-2-yl)boronic acid, CAS 32316-92-0, also known as 2-naphthaleneboronic acid, is an aromatic organoboron compound featuring a boronic acid group attached to the 2-position of a naphthalene ring. Its fused bicyclic aromatic structure provides an extended π-conjugated framework, while the boronic acid functionality offers a versatile reaction site for carbon–carbon bond formation. It is widely useful as a building block in palladium-catalyzed Suzuki–Miyaura cross-coupling reactions, enabling the introduction of a naphthyl group into more complex molecular structures. Its combination of aromatic character and synthetic versatility makes it relevant to pharmaceutical research, specialty chemical development, and functional organic materials.
Chemical Identifiers
| InChI | 1S/C10H9BO2/c12-11(13)10-6-5-8-3-1-2-4-9(8)7-10/h1-7,12-13H |
| InChI Key | KPTRDYONBVUWPD-UHFFFAOYSA-N |
| Smiles | C1=CC2=C(C=C1)C=C(C=C2)B(O)O |
| EC No. | 628-070-3 |
| MDL No. | MFCD00236051 |
| PubChem CID | 2734375 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
(Naphthalen-2-yl)boronic acid is a useful building block in medicinal chemistry and pharmaceutical intermediate development. Through Suzuki–Miyaura cross-coupling with suitable aryl or heteroaryl halides, it enables the formation of carbon–carbon bonds and the preparation of biaryl structures containing a naphthalene unit. Naphthyl groups are frequently incorporated into drug discovery compounds to explore molecular shape, hydrophobic interactions, and structure–activity relationships. This compound therefore supports the synthesis of diverse aromatic intermediates and candidate molecules for pharmaceutical research.
Applications in Biaryl and Heteroaryl Synthesis
The boronic acid group allows (Naphthalen-2-yl)boronic acid to participate in cross-coupling reactions with compatible organic electrophiles. By selecting different aryl or heteroaryl coupling partners, chemists can prepare a wide range of substituted naphthalene derivatives and extended biaryl structures. These products can serve as intermediates for further functionalization or as components of more complex molecular frameworks. The defined 2-naphthyl substitution pattern is particularly useful when precise aromatic connectivity is required in synthetic route design.
Applications in Organic Electronic Materials
The extended conjugated structure of the naphthalene ring makes this compound relevant to the synthesis of functional organic molecules for materials research. Through cross-coupling reactions, the naphthyl unit can be incorporated into larger π-conjugated frameworks that may be investigated for their optical and electronic properties. Such derivatives can be explored in organic semiconductors, optoelectronic materials, and other conjugated molecular systems. The ability to introduce different aromatic partners provides flexibility for adjusting molecular architecture and studying structure–property relationships.
Applications in Specialty Chemicals and Functional Molecules
(Naphthalen-2-yl)boronic acid is also useful in the development of specialty aromatic compounds and customized organic intermediates. Its naphthalene framework provides a rigid, fused-ring structure, while the boronic acid group enables further molecular construction through suitable coupling chemistry. This combination supports the preparation of substituted naphthyl compounds for research and industrial development. It can also serve as a starting material for synthetic strategies involving the extension or modification of aromatic molecular frameworks.
