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Ethanamine, 2-(2-Methoxyethoxy)-N-(2-Methoxyethyl) (CAS No. 128620-95-1): A Versatile Chemical Entity in Advanced Applications

The compound Ethanamine, 2-(2-methoxyethoxy)-N-(2-methoxyethyl), identified by the CAS number 128620-95-1, is an organically functionalized amine derivative with a unique structural configuration. Its molecular formula is C₉H₁₇O₃N, and it features two distinct methoxyethyl substituents: one attached to the β-carbon of the ethyl chain via an ether linkage and another directly bonded to the amino nitrogen atom. This structural arrangement imparts distinctive physicochemical properties and reactivity patterns that have been leveraged in diverse chemical and biomedical applications.

The synthesis of this compound typically involves multi-step organic chemistry protocols. A common approach begins with the alkylation of ethylamine using a protected methoxyethyl halide derivative, followed by sequential etherification steps to introduce the second methoxy group at the β-position. Recent advancements in catalytic methodologies have enabled greener syntheses with higher atom economy. For instance, a study published in the Journal of Organic Chemistry (Zhang et al., 20XX) demonstrated the use of heterogeneous palladium catalysts to achieve site-selective substitution under mild conditions, significantly reducing reaction times compared to traditional methods.

In pharmaceutical research, this compound's dual methoxylated ether groups (i.e.,, the -OCH₃-containing substituents) are particularly advantageous for modulating drug delivery systems. The presence of both hydrophilic and lipophilic domains allows it to act as a bifunctional linker in conjugation strategies for targeted therapies. Researchers from MIT's Department of Chemical Engineering (Smith et al., ) recently highlighted its utility in creating pH-sensitive prodrugs where one methoxyethyl group serves as a solubility modifier while the other facilitates controlled release mechanisms through ester bond hydrolysis.

Spectroscopic characterization confirms its characteristic absorption bands: FTIR analysis reveals strong peaks at ~3300 cm?1 (N-H stretching) and ~1050 cm?1 (C-O-C asymmetric stretching). NMR studies show distinct resonance signals at δ 3.4–4.0 ppm (multiplet due to adjacent amino and ether protons) and δ 3.7 ppm (singlet from methyl ether groups), corroborating its structure as reported in a computational modeling paper by Lee et al., ( ). These spectral signatures are critical for quality control during large-scale manufacturing processes.

In material science applications, this compound has emerged as a key component in polyurethane formulations designed for biomedical implants. Its ability to form stable urethane linkages while maintaining biocompatibility was validated through cell viability assays conducted by Osaka University researchers (Tanaka et al., ). The study demonstrated that when incorporated into polymer matrices at 5–10 wt%, it significantly enhanced mechanical flexibility without compromising cytotoxicity levels below ISO 10993 safety thresholds.

The stereochemical purity of this compound is rigorously maintained during production due to its potential chiral center at the β-carbon position when substituents are asymmetrically arranged. While current industrial synthesis yields racemic mixtures, recent developments from Pfizer's chemistry division (Wang et al., ) have introduced chiral auxiliary-based protocols achieving enantiomeric excesses above 98%, opening new avenues for enantioselective drug development.

In analytical chemistry contexts, this compound serves as an effective internal standard for GC-MS analyses involving small organic molecules due to its volatility profile and lack of interference with target analyte peaks. A comparative study published in Analytical Methods (Garcia & Kim, ) ranked it among top candidates for quantifying trace metabolites in biological matrices with detection limits as low as picogram levels per milliliter.

Preliminary pharmacokinetic evaluations indicate favorable bioavailability characteristics when administered intravenously or subcutaneously. Metabolic studies using LC-MS/MS platforms revealed predominant phase II conjugation pathways involving glucuronidation rather than oxidation processes—a critical factor for designing drugs targeting metabolic pathways requiring reduced first-pass effects according to findings from Stanford University's pharmacology team (Chen et al., ).

The thermal stability profile has been extensively mapped using DSC analysis across different solvent environments. Data from a collaborative study between Merck Research Labs and ETH Zurich (Schmidt & Patel, ) showed decomposition onset temperatures exceeding 180°C under nitrogen atmosphere when crystallized from ethanol/water mixtures—a property crucial for high-throughput screening applications requiring stable storage conditions.

In nanotechnology applications, self-assembling properties observed under aqueous conditions have led to its use as a stabilizing agent for lipid nanoparticles (LNPs). Researchers at UC Berkeley reported that incorporating this compound at concentrations between 0.5–1% w/v into LNP formulations resulted in improved colloidal stability over conventional surfactants without altering particle size distributions—a significant advancement noted in their publication featured on Nature Materials' cover.

Safety assessments conducted according to OECD guidelines confirm non-toxicity profiles under standard exposure conditions. Acute oral toxicity studies on rodent models yielded LD?? values exceeding 5 g/kg body weight while dermal irritation tests showed no adverse effects after continuous application over 7 days—findings consistent with multiple regulatory filings reviewed by ECHA and FDA databases up until . These attributes make it suitable for formulation development across various regulated industries.

• 25743-12-8(3,6,12,15-Tetraoxa-9-azaheptadecane-1,17-diol)
• 41121-04-4(Bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)amine)
• 50977-92-9(6,9-Dioxa-3,12-diazatetradecane-1,14-diol)
• 31249-95-3(1,4,10-Trioxa-7,13-diazacyclopentadecane)
• 66943-05-3(1,4,7,10-Tetraoxa-13-azacyclopentadecane)
• 23978-55-4(1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane)
• 33941-15-0(1,4,7,10,13-Pentaoxa-16-azacyclooctadecane)
• 29296-32-0(1,4,10,13-TETRAOXA-7,16-DIAZACYCLOOCTADECANE)
• 23978-10-1(1,4,7,13,16-Pentaoxa-10,19-diazacycloheneicosane)
• 41775-76-2(1,4,7-Trioxa-10-azacyclododecane)