[1,1'-Biphenyl]-4-ylmethyl acrylate
[CAS# 54140-58-8]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: [1,1'-Biphenyl]-4-ylmethyl acrylate
• Synonyms: (4-phenylphenyl)methyl prop-2-enoate
• Molecular Formula: C₁₆H₁₄O₂
• Molecular Weight: 238.28
• CAS Registry Number: 54140-58-8
• SMILES: C=CC(=O)OCC1=CC=C(C=C1)C2=CC=CC=C2

Discovory and Applicatios

[1,1'-Biphenyl]-4-ylmethyl acrylate is a synthetic organic compound consisting of an acrylate ester functional group bonded to a \[1,1'-biphenyl]-4-ylmethyl moiety. Structurally, it features a biphenyl core—a pair of benzene rings connected via a single bond—substituted at the para-position (4-position) of one ring by a methylene bridge, which in turn links to an acrylate group through an ester linkage. The acrylate portion includes a vinyl group conjugated to a carboxylic acid derivative, making the molecule suitable for polymerization reactions.

The compound is primarily known for its utility in polymer chemistry, especially in the design of functional monomers used for copolymerization with other acrylic derivatives. The vinyl group in the acrylate moiety enables free radical polymerization, a widely used method for synthesizing high molecular weight polymers. \[1,1'-Biphenyl]-4-ylmethyl acrylate has been explored as a monomer that imparts rigidity, hydrophobicity, and aromatic character to polymer backbones due to the presence of the biphenyl group.

One of the notable features of this molecule is its ability to influence the thermal and mechanical properties of the resulting polymers. The biphenyl unit contributes to increased glass transition temperature (T_g) and thermal stability, owing to its planar and rigid aromatic structure. Polymers incorporating this monomer have been studied for applications in coatings, adhesives, optical materials, and specialty resins where dimensional stability and heat resistance are required.

The presence of the biphenyl moiety also affects the optical and electronic characteristics of polymers. Biphenyl-containing monomers are often used in the development of photoresist materials, liquid crystal polymers, and dielectric films. The extended conjugation and molecular alignment properties of biphenyl structures make them suitable for use in optoelectronic devices and display technologies.

In addition, \[1,1'-biphenyl]-4-ylmethyl acrylate has been examined in the context of molecular imprinting and surface functionalization. Its aromatic content allows for π–π interactions with template molecules, which can be advantageous in designing selective recognition sites in molecularly imprinted polymers (MIPs). These materials are used for applications such as sensors, drug delivery, and chromatographic separation.

The synthesis of \[1,1'-biphenyl]-4-ylmethyl acrylate typically involves the esterification of \[1,1'-biphenyl]-4-ylmethanol with acryloyl chloride or acrylic acid in the presence of a suitable base such as triethylamine or pyridine, under controlled anhydrous conditions. The reaction proceeds via nucleophilic acyl substitution to yield the acrylate ester. Care must be taken to avoid polymerization of the acrylate during synthesis, which is typically achieved by working under cold and inert conditions with inhibitors like hydroquinone.

Analytical methods used to characterize this compound include nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry (MS). The acrylate group shows characteristic IR absorptions due to the carbon–carbon double bond and ester carbonyl stretch, while NMR spectra reveal the chemical shifts of aromatic protons, the methylene bridge, and vinyl hydrogens.

In summary, \[1,1'-biphenyl]-4-ylmethyl acrylate is a functional acrylate monomer valued for its ability to introduce aromatic rigidity and thermal stability into polymer systems. It is primarily used in advanced polymer applications such as coatings, electronics, and functional materials, where its unique structural properties contribute to performance and durability.