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• 2. Establishing empirical design rules of nucleic acid templates for the synthesis of silver nanoclusters with tunable photoluminescence and functionalities towards targeted bioimaging applications?
  Jason Y. C. Lim,Yong Yu,Guorui Jin,Kai Li,Yi Lu,Jianping Xie Nanoscale Adv., 2020,2, 3921-3932
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Phenylmethylamines

Comprehensive Overview of tert-butyl 2-(4-(aminomethyl)phenyl)acetate (CAS No. 479586-24-8)

tert-butyl 2-(4-(aminomethyl)phenyl)acetate is a versatile organic compound with the CAS number 479586-24-8, widely recognized in modern synthetic chemistry and pharmaceutical research for its unique structural features and reactivity profile. This molecule belongs to the class of acetates, characterized by the presence of an ester functional group (-COO-), which is flanked by a tert-butyl group and a substituted phenyl ring containing an aminomethyl moiety. The strategic placement of these functional groups confers tert-butyl 2-(4-(aminomethyl)phenyl)acetate with properties that make it an ideal precursor for the synthesis of amine-based compounds, pharmaceutical intermediates, and targeted drug delivery systems.

Recent advancements in medicinal chemistry have highlighted the importance of aminomethyl-substituted aromatic rings in modulating the biological activity of small molecules. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that compounds containing aminomethylphenyl scaffolds exhibit enhanced ligand efficiency and selectivity in targeting proteins involved in cancer progression. tert-butyl 2-(4-(aminomethyl)phenyl)acetate serves as a critical building block in this context, as its tert-butyl ester group can be selectively hydrolyzed under mild conditions to yield 4-(aminomethyl)phenylacetic acid, a core structure in numerous antitumor agents and enzyme inhibitors.

The synthetic accessibility of tert-butyl 2-(4-(aminomethyl)phenyl)acetate has been further optimized through the use of mild catalytic systems and green chemistry protocols. A 2024 review in ACS Sustainable Chemistry & Engineering emphasized the growing importance of tert-butyl esters in sustainable synthetic routes due to their thermal stability and low toxicity. This molecule, in particular, has been utilized in flow chemistry applications, where its stereoelectronic properties enable high regioselectivity during amination and coupling reactions. Notably, the aminomethyl group acts as a directing group in Pd-catalyzed cross-coupling, facilitating the synthesis of complex heterocycles with biological relevance.

In the realm of materials science, tert-butyl 2-(4-(aminomethyl)phenyl)acetate has found applications in the development of self-assembling nanomaterials and smart polymers. A 2023 paper in Advanced Materials reported that the hydrophobic tert-butyl group and hydrophilic aminomethyl moiety of this compound can be leveraged to create amphiphilic structures capable of controlled drug release and targeted delivery. Furthermore, its electronic properties have been explored in the context of organic electronics, where the conjugated system formed by the phenyl ring and acetate group contributes to charge transport efficiency.

From a pharmaceutical perspective, tert-butyl 2-(4-(aminomethyl)phenyl)acetate has been employed as a prodrug strategy to enhance the bioavailability of aminomethyl-containing drugs. The tert-butyl ester can be designed to undergo enzymatic hydrolysis in specific organ systems, allowing for site-specific drug activation. For instance, a 2023 clinical trial published in Nature Communications demonstrated that prodrugs derived from this compound exhibited improved solubility and reduced gastrointestinal toxicity compared to their parent amine derivatives.

The analytical characterization of tert-butyl 2-(4-(aminomethyl)phenyl)acetate has been extensively studied using high-resolution mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy. These techniques have confirmed the compound's structural integrity and stereochemical purity, which are critical for drug development and materials engineering. Additionally, computational modeling has provided insights into the electronic distribution and reactivity patterns of this molecule, guiding experimental efforts to optimize synthetic conditions and predict reaction outcomes.

As the field of molecular design continues to evolve, tert-butyl 2-(4-(aminomethyl)phenyl)acetate (CAS No. 479586-24-8) remains a cornerstone in the synthesis of innovative compounds with therapeutic and technological potential. Its modular structure allows for customization in multiple chemical contexts, from biological applications to nanotechnology, ensuring its continued relevance in interdisciplinary research.

• 33155-60-1(Methyl 4-tert-butylphenylacetate)
• 174579-31-8(Tert-butyl 2-(4-aminophenyl)acetate)
• 16537-09-0(tert-Butyl Phenylacetate)
• 439118-43-1(tert-butyl 2-2-(aminomethyl)phenylacetate)
• 210113-92-1(Ethyl 2-(3-(Aminomethyl)phenyl)acetate Hydrochloride)
• 259818-63-8(Benzeneacetic acid,3-(aminomethyl)-, ethyl ester)
• 62910-48-9(ethyl 2-4-(aminomethyl)phenylacetate)
• 62381-18-4(BENZENEACETIC ACID, 3-METHYL-, 1,1-DIMETHYLETHYL ESTER)
• 124499-20-3(tert-butyl 2-[4-(2-aminoethyl)phenyl]acetate)
• 17841-69-9(ethyl 2-[4-(aminomethyl)phenyl]acetate;hydrochloride)