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Purchase Bulk Order 1-Naphthaleneboronic acid丨CAS 13922-41-3
1-Naphthaleneboronic acid, CAS 13922-41-3, also known as naphthalene-1-boronic acid, is an aromatic organoboron compound featuring a boronic acid group attached to the 1-position of a naphthalene ring. Its fused bicyclic aromatic structure provides an extended conjugated framework, while the boronic acid functionality offers a versatile reaction site for carbon–carbon bond formation. It is particularly useful in palladium-catalyzed Suzuki–Miyaura cross-coupling reactions with suitable organic electrophiles, enabling the preparation of diverse substituted aromatic compounds. Compared with its 2-naphthyl isomer, the 1-position substitution pattern provides distinct steric and structural characteristics that can influence reaction behavior and the properties of resulting products.
Chemical Identifiers
| InChI | 1S/C10H9BO2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7,12-13H |
| InChI Key | HUMMCEUVDBVXTQ-UHFFFAOYSA-N |
| Smiles | C1=CC=C2C(=C1)C(=CC=C2)B(O)O |
| EC No. | 604-119-4 |
| MDL No. | MFCD00019722 |
| PubChem CID | 254532 |
Applications
Applications in Pharmaceutical Intermediate Synthesis
1-Naphthaleneboronic acid is a useful building block in medicinal chemistry and pharmaceutical intermediate development. Through Suzuki–Miyaura cross-coupling with compatible aryl or heteroaryl halides, it enables the introduction of a 1-naphthyl group into more complex molecular structures. Naphthalene-containing frameworks are frequently explored in drug discovery because their rigid aromatic structures and hydrophobic characteristics can influence molecular interactions and structure–activity relationships. This compound supports the synthesis of diverse biaryl intermediates and candidate molecules for pharmaceutical research.
Applications in Heterocyclic Compound Synthesis
The boronic acid group makes 1-Naphthaleneboronic acid suitable for cross-coupling reactions with a range of compatible aromatic and heteroaromatic electrophiles. It provides a convenient route to 1-substituted naphthalene derivatives and extended biaryl structures. The substitution at the 1-position creates a distinct molecular geometry compared with 2-naphthaleneboronic acid, offering additional options for controlling the orientation and steric environment of aromatic groups. These characteristics are valuable in molecular design, synthetic route development, and the preparation of structurally diverse compounds.
Applications in Organic Electronic Materials
The fused aromatic structure of 1-Naphthaleneboronic acid makes it relevant to the synthesis of extended π-conjugated molecules for materials research. Through suitable cross-coupling reactions, the naphthyl unit can be incorporated into larger aromatic frameworks that may be investigated for their optical and electronic properties. Such derivatives can be explored in organic semiconductors, optoelectronic materials, and functional organic molecules. Its defined 1-naphthyl structure provides a useful starting point for studying how molecular connectivity and steric effects influence material characteristics.
Applications in Specialty Chemicals and Functional Molecules
1-Naphthaleneboronic acid can support the development of specialty aromatic compounds and customized organic intermediates. Its rigid fused-ring framework provides a distinctive structural unit, while the boronic acid group enables further molecular construction through carbon–carbon coupling chemistry. The resulting naphthyl derivatives can be used as intermediates for additional functionalization or incorporated into more complex molecular architectures. This versatility makes the compound useful in specialty chemical research and advanced organic synthesis.
