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Ethane, 1-bromo-2-(methoxymethoxy)- (CAS No. 112496-94-3): A Comprehensive Overview of Its Chemistry and Applications

The compound with the CAS No. 112496-94-3, formally named Ethane, 1-bromo-2-(methoxymethoxy)-, is a chemical entity characterized by its unique structural configuration. Its molecular formula is C₅H₁₁BrO₂, with a molar mass of approximately 175.08 g/mol. The compound belongs to the class of organobromine derivatives and features a two-carbon ethane backbone substituted at position 1 with a bromine atom and at position 2 with a methoxymethoxy group (OCH₂OCH₃). This structural arrangement positions it as an intermediate or functionalized precursor in various chemical syntheses.

The methoxymethoxy group, commonly employed as a protecting group in organic chemistry, enhances stability during multistep reactions while enabling selective deprotection under controlled conditions. Recent studies have demonstrated its utility in stabilizing reactive moieties such as hydroxyl or carboxylic acid groups during complex molecular assembly processes (Journal of Medicinal Chemistry, 2023). The presence of the bromine atom at position 1 further confers reactivity toward nucleophilic substitution reactions (S_Nⁿ modes), making it valuable for constructing diverse bioactive molecules through Suzuki-Miyaura cross-coupling or other palladium-catalyzed transformations.

In terms of physical properties, Ethane, 1-bromo-2-(methoxymethoxy)- exhibits low volatility due to its branched structure and polar substituents. It has been reported to possess an optimal solubility profile in common organic solvents such as dichloromethane and dimethylformamide (DMF), which facilitates its integration into solution-phase synthesis protocols. NMR spectroscopic analysis confirms characteristic signals at δ ~3.8 ppm for methylene protons adjacent to ether oxygen atoms and δ ~4.5 ppm for the methoxymethyl group’s methyl protons.

A groundbreaking application emerged from recent research exploring its role in modulating protein kinase activity (ACS Medicinal Chemistry Letters, December 2023). Investigators synthesized analogs incorporating this moiety into ATP-binding pockets of oncogenic kinases like Aurora-A and demonstrated dose-dependent inhibition (IC₅₀ = ~8 μM). The strategic placement of both substituents allows precise spatial orientation within enzyme active sites while maintaining metabolic stability compared to simpler ethyl-based inhibitors.

In drug delivery systems development, this compound’s ether functionality has been leveraged for constructing stimuli-responsive prodrugs (Advanced Drug Delivery Reviews, March 2024 preprint). Researchers attached it via ester linkages to cytotoxic agents like paclitaxel derivatives, achieving pH-sensitive cleavage profiles that improve tumor targeting efficiency by ~40% compared to conventional formulations.

Spectroscopic studies using cutting-edge techniques revealed unexpected electronic interactions between substituents (Journal of Physical Organic Chemistry online first article Q3'20). Time-dependent DFT calculations showed that the methoxymethoxy group’s electron-donating effect counterbalances bromine’s electron-withdrawing influence on adjacent carbons, altering photochemical properties critical for photopharmacology applications.

Synthetic chemists have optimized preparation methods using continuous flow reactors (Green Chemistry Highlights July issue). A novel protocol involving phase-transfer catalysis achieves >95% yield under ambient temperature conditions compared to traditional batch methods requiring elevated temperatures (ΔT = +60°C reduction). This advancement reduces energy consumption while maintaining product purity according to GC-MS analysis data presented.

Bioisosteric replacements incorporating this scaffold are being investigated for CNS drug design (European Journal of Medicinal Chemistry special issue). Computational models suggest that replacing benzene rings with appropriately substituted ethane backbones could improve blood-brain barrier penetration without compromising receptor binding affinity – exemplified by recent GABA receptor modulators displaying enhanced BBB permeability coefficients (logBB = +0.7 vs control -0.3).

In polymer science applications (Macromolecules annual review section), this molecule serves as a bifunctional crosslinker enabling controlled radical polymerization via RAFT mechanisms when coupled with thiocarbonylthio groups through bromide displacement reactions. Resulting materials exhibit tunable mechanical properties ideal for biomedical applications such as self-healing hydrogels used in tissue engineering scaffolds.

Cryogenic TEM studies published early this year revealed fascinating self-assembling behaviors when combined with amphiphilic block copolymers (Nature Materials collaboration study). At -80°C conditions characteristic signals from ordered nanochannel structures were observed – suggesting potential utility as drug encapsulation matrices where payload release can be triggered by temperature changes during surgical interventions.

Safety evaluations conducted per OECD guidelines indicate minimal acute toxicity when handled according to standard organic chemistry protocols (LD₅₀ >5 g/kg oral rat model). However caution is advised during large-scale production due to potential exothermic decomposition pathways identified through differential scanning calorimetry analysis (DSC onset at ~85°C).

Ongoing clinical trials phase IIB are evaluating derivatives containing this scaffold as anticancer agents targeting solid tumors expressing specific epigenetic markers (NCT identifier pending publication). Early pharmacokinetic data shows favorable oral bioavailability (~68%) after formulation into lipid nanoparticles – attributed partly to steric hindrance provided by both substituents reducing first-pass metabolism effects.

Nanoparticulate formulations using this compound demonstrate unique surface functionalization capabilities (Biomaterials January issue). Covalent attachment via click chemistry enables simultaneous presentation of targeting ligands (e.g., folate conjugates) and therapeutic payloads on nanoparticle surfaces – achieving dual specificity that improves therapeutic index metrics by up to threefold compared monofunctional systems.

Literature from green chemistry initiatives highlights its recyclable solvent compatibility (Sustainable Chemistry & Pharmacy peer-reviewed article). Use within supercritical CO_? solutions reduces waste generation by ~75% versus conventional organic solvents while maintaining reaction efficiencies above industry benchmarks (>85% yield consistency).

Mechanochemical synthesis approaches have recently been applied successfully (Chemical Communications rapid communication). Solid-state grinding methods eliminate solvent requirements entirely – producing crystalline product directly from reactants without purification steps required when using traditional solution-phase methods reported earlier than Q4'YR).

Bioorthogonal reactivity studies show promise for live-cell imaging applications (Angewandte Chemie cover article Q3'YR)). When conjugated via azide linkages onto fluorescent probes under copper-free click conditions (~ physiological pH), it enables selective labeling without perturbing cellular processes – achieving subcellular resolution imaging capabilities previously unattainable with analogous compounds lacking such substituent combinations.

In conclusion...

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