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Comprehensive Guide to 1-Phenyl-1-trimethylsilyloxyethylene (CAS No. 13735-81-4): Properties, Applications, and Industry Insights

1-Phenyl-1-trimethylsilyloxyethylene (CAS No. 13735-81-4) is a specialized organosilicon compound widely utilized in organic synthesis and pharmaceutical intermediates. Its unique molecular structure, featuring a phenyl group and a trimethylsilyloxy moiety, enables versatile reactivity in cross-coupling reactions and protective group chemistry. Researchers often refer to it by alternative names like 1-Phenyl-1-(trimethylsilyloxy)ethene or TMSE-protected styrene oxide, highlighting its role in advanced synthetic methodologies.

In recent years, the demand for silyl enol ether derivatives like 1-Phenyl-1-trimethylsilyloxyethylene has surged due to their applications in asymmetric catalysis and green chemistry. A 2023 study published in the Journal of Organic Chemistry emphasized its efficiency in Brook rearrangements, a topic frequently searched in academic databases. The compound's stability under anhydrous conditions makes it particularly valuable for air-sensitive reactions, a common challenge discussed in synthetic chemistry forums.

The synthesis of 13735-81-4 typically involves the silylation of phenylacetylene derivatives, with yields optimized through modern techniques like flow chemistry – a trending topic in industrial process optimization. Analytical characterization via NMR spectroscopy (particularly ²⁹Si NMR) and GC-MS confirms its purity, addressing quality concerns frequently raised by procurement specialists. Notably, its low volatility compared to similar silyl ethers reduces handling risks, making it preferable for scale-up operations.

From an application perspective, 1-Phenyl-1-trimethylsilyloxyethylene serves as a key precursor for β-hydroxy carbonyl compounds through Mukaiyama aldol reactions. Pharmaceutical developers increasingly search for its use in chiral auxiliaries for antihistamine synthesis, as evidenced by patent filings. Material scientists also explore its potential in silicon-containing polymers, correlating with the growing interest in hybrid organic-inorganic materials for flexible electronics.

Storage recommendations for CAS 13735-81-4 emphasize argon atmosphere preservation at -20°C, a detail often queried by laboratory managers. Suppliers should note that packaging under nitrogen purge significantly extends shelf life, a best practice highlighted in recent chemical logistics webinars. Market analysis indicates rising procurement of this compound by Asian research hubs, reflecting regional growth in fine chemical production capabilities.

Environmental considerations position trimethylsilyloxy-functionalized compounds as greener alternatives to traditional protecting groups due to their hydrolytic degradability. This aligns with the pharmaceutical industry's focus on PMI reduction (Process Mass Intensity), a metric dominating sustainability discussions. Computational chemistry studies of 13735-81-4, particularly DFT calculations of its HOMO-LUMO gap, provide theoretical insights frequently cited in quantum chemistry publications.

For analytical laboratories, HPLC methods using C18 reverse-phase columns with acetonitrile/water gradients effectively separate 1-Phenyl-1-trimethylsilyloxyethylene from byproducts. Method development protocols for this compound are increasingly shared on open science platforms, responding to the research community's demand for reproducible procedures. Its UV absorption at 254 nm facilitates convenient detection, a practical advantage noted in method optimization guides.

Emerging applications in photoredox catalysis leverage the compound's electron-rich vinyl group, a research direction gaining traction in synthetic methodology papers. The compound's role in constructing quaternary carbon centers – a persistent challenge in total synthesis – has been featured in recent conference proceedings, making it a subject of academic curiosity. These developments position CAS 13735-81-4 as a multifaceted tool for molecular complexity generation in modern organic chemistry.

• 503839-04-1(Silane, trimethyl[[1-(4-pentylphenyl)ethenyl]oxy]-)
• 54731-27-0(Silane, trimethyl[[1-(4-methylphenyl)ethenyl]oxy]-)
• 58518-77-7(Silane, [[1-(4-fluorophenyl)ethenyl]oxy]trimethyl-)
• 55991-66-7(Silane, [[1-(4-bromophenyl)ethenyl]oxy]trimethyl-)
• 66323-99-7(Silane, trimethyl[(1-phenyl-1-propenyl)oxy]-, (Z)-)
• 88089-52-5(Silane, [(1,2-diphenylethenyl)oxy]trimethyl-, (Z)-)
• 59790-58-8(Silane, trimethyl[[1-(3-methylphenyl)ethenyl]oxy]-)
• 37471-46-8(Silane, trimethyl[(1-phenyl-1-propenyl)oxy]-)
• 61668-33-5(Silane, [(2-bromo-1-phenylethenyl)oxy]trimethyl-)
• 139885-59-9(Silane, trimethyl[[1-(2,4,5-trimethylphenyl)ethenyl]oxy]-)