CAS 96857-55-5, Cat. No EN300-717237
Reagent for fluorination
Diethyl fluoromethylphosphonate is a reagent used for synthesizing α-fluoro-β-ketophosphonates via LDA-mediated condensation with esters under mild conditions. It avoids issues common in electrophilic fluorination, offering high selectivity for monofluorinated products1. In medicinal chemistry, its derivatives act as phosphatase-resistant phosphate mimics, useful for studying lipid signaling pathways such as PI3P metabolism2. The reagent’s stability and broad reactivity make it a valuable tool in both synthetic and biological applications.
Synonyms: diethyl (fluoromethyl)phosphonate; 1-[ethoxy(fluoromethyl)phosphoryl]oxyethane; fluoromethyl-phosphonic acid diethyl ester; diethyl fluoromethylphosphonate
Selected publications
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Condensation of Diethyl Fluoromethylphosphonate with Esters: An Alternative Synthetic Route to Diethyl α-Fluoro-β-Ketophosphonates.
Tarasenko, K. V.; Romanenko, V. D.; Sorochinsky, A. E. J Fluor Chem 2018, 211, 124–128. DOI: 10.1016/j.jfluchem.2018.04.014
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Chemical Synthesis and Molecular Recognition of Phosphatase-Resistant Analogues of Phosphatidylinositol-3-Phosphate.
Xu, Y.; Lee, S. A.; Kutateladze, T. G.; Sbrissa, D.; Shisheva, A.; Prestwich, G. D. J Am Chem Soc 2006, 128 (3), 885–897. DOI: 10.1021/ja0554716