• 1. Examination of the hydrogen-bonding networks in small water clusters (n = 2–5, 13, 17) using absolutely localized molecular orbital energy decomposition analysis?
  Erika A. Cobar,Paul R. Horn,Robert G. Bergman,Martin Head-Gordon Phys. Chem. Chem. Phys., 2012,14, 15328-15339
• 2. Estimates of hydride ion stability in condensed systems: energy of formation and solvation in aqueous and polar-organic solvents
  Craig A. Kelly,David R. Rosseinsky Phys. Chem. Chem. Phys., 2001,3, 2086-2090
• 3. Excimer emission and magnetoluminescence of radical-based zinc(ii) complexes doped in host crystals?
  Shojiro Kimura,Tetsuro Kusamoto Chem. Commun., 2020,56, 11195-11198
• 4. Excellent energy storage performance in NaNbO3-based relaxor antiferroeic ceramics under a low electric field
  XuxinCheng,XiaomingChen,PengyuanFan
• 5. Enabling stable MnO2 matrix for aqueous zinc-ion battery cathodes?
  Yiding Jiao,Liqun Kang,Jasper Berry-Gair,Kit McColl,Jianwei Li,Haobo Dong,Hao Jiang,Ryan Wang,Furio Corà,Dan J. L. Brett,Ivan P. Parkin J. Mater. Chem. A, 2020,8, 22075-22082

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Aminobenzoic acids and derivatives
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Aminobenzoic acids and derivatives

4-Amino-2-Methylbenzamide: Chemical Properties, Synthesis, and Emerging Applications

4-Amino-2-methylbenzamide, identified by the CAS registry number 52771-13-8, is an organic compound with the molecular formula C₈H₉NO₂. Its structure comprises a benzene ring substituted with an amino group at the 4-position and a methyl group at the 2-position, coupled with a carboxamide functional group. This configuration confers unique physicochemical properties and reactivity, making it a versatile building block in medicinal chemistry and materials science. Recent advancements in synthetic methodologies and biological applications have positioned 4-amino-2-methylbenzamide as a compound of growing interest in academic and industrial research.

The synthesis of 4-amino-2-methylbenzamide has evolved significantly over the past decade. Traditional approaches involved nitration followed by reduction and amidation steps, which often required harsh conditions. However, recent studies published in Tetrahedron Letters (Smith et al., 2023) demonstrated a greener one-pot synthesis using microwave-assisted conditions with heterogeneous catalysts. This method reduces reaction time from hours to minutes while minimizing solvent usage, aligning with current sustainability trends in chemical manufacturing. Another notable development comes from Journal of Organic Chemistry, where researchers utilized enzymatic catalysis to achieve high stereoselectivity in its preparation as part of asymmetric drug intermediates (Chen & Wang, 2023). These innovations highlight the compound's adaptability to modern synthetic strategies aimed at improving efficiency and environmental compatibility.

In pharmaceutical research, 4-amino-2-methylbenzamide serves as a critical intermediate in the development of anti-inflammatory agents. A groundbreaking study in Nature Communications (Lee et al., 2023) revealed its ability to modulate cyclooxygenase (COX) enzymes when conjugated with bioactive moieties. The compound's amide group facilitates bioisosteric replacement in COX inhibitor designs, offering potential for reduced gastrointestinal side effects compared to conventional NSAIDs. Furthermore, its amino substituent enables facile conjugation with targeting ligands for site-specific drug delivery systems, as evidenced by recent work on tumor-penetrating peptides reported in Bioconjugate Chemistry.

Beyond drug design, this compound exhibits intriguing photochemical properties that are being explored for diagnostic applications. A 2023 paper in Analytical Chemistry described its use as a fluorescent probe for real-time monitoring of intracellular pH changes in live cells. The methyl substitution enhances stability under physiological conditions while maintaining tunable emission spectra when combined with metal complexes or fluorophores through click chemistry modifications. Such properties make it an attractive candidate for developing next-generation biosensors capable of non-invasive cellular analysis.

The structural flexibility of 4-amino-2-methylbenzamide also supports its role in advanced materials research. When incorporated into polymer matrices via covalent bonding techniques outlined in Polymer Chemistry, it imparts piezoelectric characteristics suitable for flexible electronic devices. Recent studies have demonstrated that derivatives synthesized through Suzuki-Miyaura coupling reactions exhibit enhanced charge storage capabilities when used as components in organic solar cells (Kumar et al., 2023). These findings underscore the compound's potential across diverse technological applications.

In biochemical contexts, this compound has been shown to interact uniquely with protein targets through π-stacking interactions due to its aromatic backbone. A collaborative study between MIT and Stanford researchers (published in JACS Au, 2023) identified specific binding affinity for histone deacetylase enzymes when functionalized with hydroxamic acid groups. This discovery opens new avenues for epigenetic therapy development where precise enzyme modulation is required without off-target effects.

Epidemiological studies suggest that structurally similar compounds may have neuroprotective effects based on their ability to inhibit amyloid beta aggregation (Journal of Alzheimer's Disease, 2023). While direct evidence for CAS No 56771-13-8's role remains limited at present, computational docking studies indicate favorable binding profiles toward key Alzheimer's-related targets such as BACE1 protease inhibitors.

Safety evaluations conducted under OECD guidelines (OECD Test Guideline No: 451) confirm its low acute toxicity profile when handled according to standard laboratory protocols. Recent toxicokinetic studies published in Toxicological Sciences,

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