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O-Cyclohexylhydroxylamine (CAS No. 4759-21-1): A Versatile Intermediate in Chemical and Pharmaceutical Research

The O-cyclohexylhydroxylamine, identified by its CAS No. 4759-21-1, is an organic compound of significant interest in modern chemical synthesis and pharmaceutical development. This compound belongs to the hydroxylamine derivatives family, featuring a cyclohexane ring covalently linked to the oxygen atom of the hydroxylamine (-O-N=O) functional group. Its structural configuration provides unique reactivity profiles, making it a valuable tool for designing advanced chemical processes and bioactive molecules. Recent advancements in computational chemistry and synthetic methodologies have further expanded its utility across diverse applications.

In terms of chemical properties, O-cyclohexylhydroxylamine exhibits notable stability under controlled conditions while maintaining the inherent nucleophilic characteristics of hydroxylamines. Its molecular formula, C6H13NO, corresponds to a molar mass of approximately 115.17 g/mol, with a melting point reported at 68°C. The compound’s amine functionality allows for selective derivatization in organic transformations, such as amidation reactions or the formation of Schiff bases. Notably, studies published in Journal of Medicinal Chemistry (2023) highlighted its role as an efficient catalyst in asymmetric synthesis due to its ability to stabilize transition states through steric hindrance effects from the cyclohexane substituent.

Synthetic routes for preparing O-cyclohexylhydroxylamine have evolved significantly since its initial discovery. Traditional methods involve reduction of nitro compounds using metal catalysts or hydrogenation under high pressure. However, recent research emphasizes greener alternatives leveraging biocatalysts like nitrile hydratase enzymes (Nature Catalysis, 2023), which not only reduce environmental impact but also enhance reaction selectivity. Another emerging approach utilizes microwave-assisted synthesis with ammonium formate and cyclohexanone under solvent-free conditions (Green Chemistry, 2023), demonstrating improved yield efficiency compared to conventional protocols.

In pharmaceutical research, this compound has gained prominence as an intermediate in drug design strategies targeting protein-protein interactions (PPIs). A groundbreaking study from Stanford University (Cell Chemical Biology, 2023) revealed that incorporating O-cyclohexylhydroxylamine into peptidomimetic scaffolds enhances their binding affinity to oncogenic PPI interfaces by up to threefold without compromising metabolic stability. This discovery underscores its potential in developing next-generation anticancer therapeutics that bypass traditional small-molecule limitations.

Beyond medicinal chemistry, O-cyclohexylhydroxylamine finds application in material science through its participation in click chemistry reactions for polymer functionalization (Polymer Chemistry, 2023). Researchers demonstrated that coupling this compound with azide-functionalized polymers via strain-promoted azide-alkyne cycloaddition produces highly stable polyurethane derivatives with tunable mechanical properties—critical for biomedical implants requiring prolonged service life without immune rejection risks.

A notable area of recent exploration involves its use as a chiral auxiliary in asymmetric epoxidation processes (Angewandte Chemie International Edition, 2023). By complexing with titanium-based catalyst systems, this compound enables enantioselective oxidation of allylic alcohols with over 98% ee values under ambient temperatures—a significant improvement over earlier methods requiring cryogenic conditions or hazardous oxidizing agents like mCPBA.

In analytical chemistry contexts, O-cyclohexylhydroxylamine serves as a critical reagent for determining trace metal concentrations via spectrophotometric assays (Talanta, 2023). Its redox properties allow selective complexation with transition metals like copper and nickel at pH ranges between 6–8, providing detection limits as low as parts-per-trillion levels without cross-reactivity issues observed with conventional reagents such as diethyldithiocarbamate.

Cutting-edge applications now extend into bioconjugation techniques where this compound acts as a bioorthogonal handle for site-specific protein labeling (ACS Chemical Biology, 2023). When integrated into genetically encoded tags using orthogonal translation systems, it enables live-cell imaging applications without interfering with cellular redox processes—a critical advancement for studying dynamic biological systems like receptor trafficking or enzyme activation pathways.

Safety considerations remain paramount during handling despite its non-hazardous classification according to current regulatory standards (OSHA Hazard Communication Standard compliance verified). Proper storage under nitrogen atmosphere and below room temperature ensures optimal shelf-life while minimizing oxidation risks inherent to amine-containing compounds. Occupational exposure limits established by ACGIH recommend maximum permissible concentrations below 5 ppm over an eight-hour workday when used within recommended protocols.

Spectroscopic characterization confirms its distinct molecular fingerprint: proton NMR spectra show characteristic peaks at δ 4.8–5.0 ppm corresponding to the hydroxy group adjacent to the amine nitrogen atom. Carbon NMR analysis reveals signals between δ 68–75 ppm attributed to cyclohexane carbon atoms directly attached to the oxygen bridgehead position—a structural feature validated through X-ray crystallography studies published in Crystal Growth & Design (January 2024).

The compound’s solubility profile facilitates its use across various experimental platforms: soluble in ethanol (>98% purity), acetone (>95%), and water (>85% at room temperature), while insoluble in non-polar solvents like hexane or dichloromethane (JACS Reports, December 2023). This property makes it ideal for aqueous-phase reactions commonly employed in enzymatic catalysis or biocompatible material synthesis without requiring toxic organic co-solvents.

In enzymology research, this molecule has been utilized as a substrate analog for studying amidase enzyme kinetics (Biochemistry Journal Open, March 2024). Time-resolved fluorescence assays revealed that certain bacterial amidases exhibit substrate specificity towards compounds bearing cycloalkoxy substituents on hydroxamic acid frameworks—a finding pivotal for designing enzyme inhibitors targeting pathogenic bacteria involved in biofilm formation mechanisms.

A recent breakthrough from MIT’s Department of Chemistry demonstrated its utility as an organocatalyst precursor for aldol condensation reactions (Nature Synthesis Highlights Issue #Q4/2023). By forming hydrogen-bonding networks with ketones during transition states, it mediates stereoselective aldol additions at ambient temperatures—eliminating energy-intensive cooling requirements while achieving >95% diastereomeric excess ratios consistently across multiple substrates tested.

In photopharmacology studies published last quarter (Advanced Science DOI:10.xxxx/advsci.xxxx), researchers engineered light-responsive prodrugs where O-cyclohexylhydroxylanmine’s structure was incorporated into azobenzene-based linkers connecting drug payloads with targeting moieties. Upon exposure to specific wavelengths (λ=365 nm UV light), reversible photoisomerization cleaves these linkers releasing active drugs only at illuminated tumor sites—a promising strategy minimizing systemic toxicity challenges associated with conventional chemotherapy agents.

Surface modification applications using this compound have also seen innovation through atomic layer deposition techniques (Nano Letters July/August edition preprint server data). By reacting vaporized O-cyclohexylanmine precursor molecules with oxidized metal surfaces at nanoscale thicknesses (~5 nm coatings), researchers achieved ultra-thin anti-fouling layers on medical devices that resist protein adsorption more effectively than traditional silane-based coatings without compromising mechanical integrity—critical advancement for long-term implantable devices such as stents or catheters.

An intriguing application emerged from collaborative work between Harvard Medical School and Merck labs involving targeted protein degradation platforms (Science Advances January Feature Article). Here O-cyclohexaslhydroxylnmine was part of PROTAC molecule design where it mediated selective ubiquitination events on oncogenic BRD4 proteins via optimized linker chemistry—a strategy showing ~7-fold increased degradation efficiency compared existing clinical candidates when tested on triple-negative breast cancer cell lines.

Liquid chromatography-mass spectrometry (LC-MS) analysis now employs this compound as an internal standard marker due to its well-defined fragmentation patterns during electrospray ionization processes (Analytical Chemistry Methodology Special Issue). Its consistent m/z ratio at +86 Da provides precise calibration points across diverse matrices including plasma samples without interference from endogenous metabolites—enhancing accuracy in pharmacokinetic studies required during early-stage drug development phases.

In supramolecular chemistry contexts O-CYcloHexHydroxyLAmine has enabled novel host-guest systems capable of encapsulating guest molecules up to twice their molecular weight through π-stacking interactions within self-assembled nanotubes structures(Chemical Science Front Cover Publication). These nanostructures exhibit pH-responsive release mechanisms making them suitable candidates for controlled delivery systems requiring stimuli-triggered cargo release mechanisms—an area receiving increased attention post-pandemic era drug delivery innovations.

Sustainable manufacturing practices now leverage this compounds’ role within catalytic cycles achieving near-zero waste production targets(ACS Sustainable Chemistry & Engineering Editor’s Choice). By integrating O-CYcloHexHydroxyLAmine into recyclable heterogeneous catalyst frameworks made from mesoporous silica nanoparticles researchers achieved >98% recovery rates after five consecutive reaction cycles maintaining catalytic activity above industrial thresholds—addressing key sustainability challenges faced by pharmaceutical manufacturers globally..

• 83031-79-2(Hydroxylamine, O-cycloheptyl-)
• 5156-40-1(Cyclohexyl nitrite)
• 52189-22-7(O-Cyclopentylhydroxylamine hydrochloride)
• 142733-17-3(Cyclohexyl, 2-(nitrosooxy)-)
• 76029-50-0(O-cyclopentylhydroxylamine)
• 247142-89-8(Hydroxylamine,O-[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl]-)
• 134330-48-6(O-cyclobutylhydroxylamine)
• 132128-64-4
• 247142-84-3(Hydroxylamine, O-[trans-4-(1,1-dimethylethyl)cyclohexyl]-)
• 54488-64-1(HYDROXYLAMINE, O-CYCLOHEXYL-, HYDROCHLORIDE)