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Bulk Inquiry (4-Pentylphenyl)boronic acid丨CAS 121219-12-3
(4-Pentylphenyl)boronic acid (CAS 121219-12-3), also known as 4-pentylbenzeneboronic acid, is an aromatic organoboron compound containing a boronic acid group and a linear pentyl substituent at the para-position of a benzene ring. The boronic acid functionality enables carbon–carbon bond formation, while the pentyl chain contributes hydrophobic characteristics and molecular flexibility. This compound is a useful building block for liquid crystal materials, functionalized biaryl compounds, organic materials research, and specialty chemical synthesis.
Chemical Identifiers
| InChI | 1S/C11H17BO2/c1-2-3-4-5-10-6-8-11(9-7-10)12(13)14/h6-9,13-14H,2-5H2,1H3 |
| InChI Key | UZRMPSOGFATLJE-UHFFFAOYSA-N |
| Smiles | CCCCCC1=CC=C(B(O)O)C=C1 |
| EC No. | 681-163-0 |
| MDL No. | MFCD00995151 |
| PubChem CID | 4589191 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
This compound serves as an organoboron coupling partner in Suzuki–Miyaura reactions for preparing alkyl-substituted biaryl and aryl–heteroaryl compounds. Under appropriately optimized palladium-catalyzed conditions, its boronic acid group reacts with compatible aromatic halides to form new carbon–carbon bonds. This transformation provides an effective route for introducing a para-pentylphenyl fragment into complex aromatic structures.
Applications in Liquid Crystal Materials
(4-Pentylphenyl)boronic acid is particularly relevant to the synthesis of liquid crystal intermediates containing alkyl-substituted aromatic structures. The linear pentyl chain can influence molecular packing, flexibility, and phase-transition behavior, while the aromatic ring contributes structural rigidity. Through suitable cross-coupling reactions, this compound can be incorporated into biphenyl and other mesogenic frameworks investigated for liquid crystal display materials and related applications.
Applications in Functionalized Biaryl Synthesis
(4-Pentylphenyl)boronic acid is useful for constructing substituted biphenyl compounds containing a flexible alkyl chain. The pentyl substituent can influence solubility, hydrophobicity, and intermolecular interactions, while the biaryl framework provides structural rigidity. These characteristics make the resulting compounds relevant to materials chemistry and the investigation of molecular structure–property relationships.
Applications in Organic Electronic Materials
Alkyl-substituted aromatic building blocks are investigated in organic electronics because alkyl chains can influence solubility, film formation, and molecular organization. (4-Pentylphenyl)boronic acid may serve as an intermediate for preparing functionalized aromatic compounds used in organic semiconductor and conjugated materials research. The performance of resulting materials depends on their complete molecular structure and processing conditions.
