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  Olga Guselnikova,Gérard Audran,Jean-Patrick Joly,Andrii Trelin,Evgeny V. Tretyakov,Vaclav Svorcik,Oleksiy Lyutakov,Sylvain R. A. Marque Chem. Sci., 2021,12, 4154-4161
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  Ziyang Deng,Changwei Chen,Sunliang Cui RSC Adv., 2016,6, 93753-93755
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• Solvents and Organic Chemicals Organic Compounds Organic nitrogen compounds Organonitrogen compounds Amines Primary amines

Comprehensive Overview of Cyclononanamine (CAS No. 59577-26-3): Properties, Applications, and Research Insights

Cyclononanamine (CAS No. 59577-26-3) is a cyclic amine compound featuring a nine-membered carbon ring with an amino functional group. This unique structure places it within the broader category of alicyclic amines, which are increasingly studied for their versatile chemical properties and potential applications in pharmaceuticals, agrochemicals, and material science. The compound's molecular formula (C9H19N) and structural specificity make it a subject of interest for researchers exploring ring strain effects and conformational dynamics in medium-sized rings.

Recent advancements in organic synthesis methodologies have reignited interest in cyclononanamine derivatives, particularly as building blocks for drug discovery and catalysis. The compound's steric profile and basicity are frequently compared to smaller cyclic amines like cyclohexylamine or larger analogs such as cyclododecylamine, offering insights into structure-activity relationships. Computational chemistry studies utilizing density functional theory (DFT) have modeled its preferred ring conformations, revealing intriguing torsional flexibility that could influence molecular recognition processes.

In material science, 59577-26-3 has been investigated as a potential ligand precursor for metal-organic frameworks (MOFs) and as a surface modifier for nanoparticles. Its amino group reactivity enables covalent bonding with carbonyl compounds, making it valuable for designing polymeric networks with tailored porosity. Environmental researchers have also examined its biodegradation pathways, with some studies suggesting slower degradation kinetics compared to linear amines due to its cyclic stability.

The pharmaceutical industry explores cyclononanamine scaffolds for bioactive molecule design, particularly in GPCR-targeting compounds where ring size influences receptor binding affinity. Patent literature reveals its incorporation into neuromodulatory agents and enzyme inhibitors, though clinical applications remain in early stages. Analytical chemists employ advanced techniques like LC-MS and NMR spectroscopy to characterize its purity and stereochemical properties, with particular attention to enantiomeric separation challenges posed by its flexible ring system.

From an industrial perspective, cyclononanamine production typically involves reductive amination of corresponding cyclic ketones or ring-closing metathesis strategies. Process optimization focuses on minimizing byproduct formation and improving atom economy, reflecting growing emphasis on green chemistry principles. Safety assessments indicate standard amine handling protocols are sufficient, though its volatility profile necessitates proper ventilation in laboratory settings.

Emerging research directions include exploring cyclononanamine-functionalized ionic liquids for CO2 capture applications and investigating its supramolecular chemistry with crown ether analogs. The compound's phase behavior in mixed solvent systems has implications for extraction processes, while its spectroscopic fingerprints aid in analytical method development for complex amine mixtures. As synthetic biology advances, engineered enzymes capable of stereoselective amination of cyclic hydrocarbons may open new production routes for this interesting molecule.

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• 3114-70-3(Cyclohexane-1,4-diamine)
• 5329-79-3(1-Methylpentylamine)
• 5452-37-9(Cyclooctylamine)
• 616-24-0(3-Aminopentane)
• 2615-25-0(trans-cyclohexane-1,4-diamine)
• 6240-90-0((R)-(?)-2-Aminoheptane)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)