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Comprehensive Overview of 4-Amino-N-benzylbenzamide (CAS No. 54977-92-3): Properties, Applications, and Research Insights

4-Amino-N-benzylbenzamide (CAS No. 54977-92-3) is a specialized organic compound that has garnered significant attention in pharmaceutical and biochemical research due to its unique structural properties. This benzamide derivative features an amino group at the para position of the benzene ring, coupled with a benzyl substituent on the amide nitrogen. Its molecular formula, C₁₄H₁₄N₂O, and molecular weight of 226.28 g/mol make it a versatile intermediate in synthetic chemistry. Researchers often explore its potential as a building block for drug discovery, particularly in designing kinase inhibitors or modulators of protein-protein interactions.

The compound's solubility profile and stability under physiological conditions are frequently discussed topics in scientific forums. Studies indicate that 4-Amino-N-benzylbenzamide exhibits moderate solubility in polar organic solvents like dimethyl sulfoxide (DMSO) and methanol, while being less soluble in water. This characteristic makes it suitable for various organic synthesis applications, where controlled reactivity is required. Recent publications highlight its role in developing fluorescence probes, leveraging the amino group's ability to participate in conjugation reactions with fluorophores.

In the context of drug development, 54977-92-3 has been investigated for its potential as a pharmacophore in neurodegenerative disease research. The benzylamide moiety provides lipophilicity, which may enhance blood-brain barrier penetration—a critical factor in central nervous system-targeted therapies. Computational studies suggest that derivatives of this compound could interact with amyloid-beta aggregates, aligning with current Alzheimer's disease research trends. These findings position 4-Amino-N-benzylbenzamide as a candidate for structure-activity relationship (SAR) studies in medicinal chemistry.

From an industrial perspective, the compound's synthetic scalability is a key consideration. Optimized routes often involve Buchwald-Hartwig amination or Ullmann-type coupling reactions, reflecting broader trends in green chemistry and catalytic process optimization. Manufacturers emphasize high-purity grades (>98%) to meet the demands of high-throughput screening platforms, where consistency is paramount. Analytical techniques like HPLC and LC-MS are routinely employed to verify the absence of byproducts such as N-benzylbenzamide or 4-nitrobenzamide precursors.

Emerging applications in material science have expanded the relevance of CAS No. 54977-92-3. Its aromatic structure contributes to the development of organic semiconductors and liquid crystal compositions. The compound's ability to form hydrogen bonds through both the amide and amino groups enables the creation of supramolecular assemblies—a hot topic in nanotechnology research. Patent literature reveals its incorporation into photoresponsive materials, where the amino group facilitates photoinduced electron transfer mechanisms.

Safety evaluations of 4-Amino-N-benzylbenzamide follow standard REACH compliance protocols. While not classified as hazardous under GHS criteria, proper handling with personal protective equipment (PPE) is recommended due to potential dust irritation. Storage typically occurs under inert atmospheres at 2-8°C to prevent oxidative degradation, a consideration shared across many amino-aromatic compounds. These protocols align with industry-wide shifts toward sustainable laboratory practices and waste minimization strategies.

The compound's spectroscopic fingerprints serve as valuable identification tools. Infrared spectroscopy typically shows characteristic stretches for the amide carbonyl (~1650 cm^-1) and primary amine (~3400 cm^-1). Nuclear magnetic resonance (NMR) spectra display distinct patterns for the benzyl protons (δ 4.4-4.6 ppm) and aromatic protons (δ 6.5-7.8 ppm), which aid in quality control. These analytical markers are crucial for researchers comparing synthetic batches or investigating metabolic transformation products in biological studies.

Market analysis indicates growing demand for 54977-92-3 across North American and Asian research hubs, driven by increased funding for precision medicine initiatives. Suppliers often provide customized isotope-labeled versions (e.g., ¹³C or ¹⁵N) for tracer studies, catering to the expanding proteomics and metabolomics sectors. This trend reflects the broader pharmaceutical industry's focus on targeted drug delivery systems and biomarker discovery platforms.

Future research directions may explore the compound's utility in click chemistry applications, particularly through azide-alkyne cycloadditions involving the amino group. Additionally, its potential as a metal-organic framework (MOF) linker could open avenues in gas storage or catalysis—areas gaining traction in renewable energy research. Such multidisciplinary applications underscore the enduring relevance of 4-Amino-N-benzylbenzamide in advancing both fundamental science and technological innovation.

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