Eschenmoser's salt
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Eschenmoser's salt | |
Names | |
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IUPAC name
Dimethylmethylideneammonium iodide
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Identifiers | |
33797-51-2 (Iodide) 30354-18-8 (Chloride) |
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ChemSpider | 2006292 ![]() |
Jmol 3D model | Interactive image Interactive image |
PubChem | 2724133 |
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Properties | |
C3H8NI | |
Molar mass | 185.01 g/mol |
Appearance | colorless hygroscopic crystals |
Melting point | 116 °C (241 °F; 389 K) |
decomposes | |
Vapor pressure | {{{value}}} |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references | |
Eschenmoser's salt, dimethylmethylideneammonium iodide, is a strong dimethylaminomethylating agent, used to prepare derivatives of the type RCH2N(CH3)2.[1][2] Enolates, enolsilylethers, and even more acidic ketones undergo efficient dimethylaminomethylation. Once prepared, such tertiary amines can be further methylated and then subjected to base-induced elimination to afford methylenated ketones. The salt was first prepared by the group of Albert Eschenmoser[3] after whom the reagent is named.
Analogous salts, dimethylmethylideneammonium chloride (Böhme's salt[1]:{{{3}}}, after Horst Böhme) and trifluoroacetate, have similar properities and applications.[1]:{{{3}}}
References
- ↑ 1.0 1.1 1.2 E. F. Kleinman in "Dimethylmethyleneammonium Iodide and Chloride" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289X.rd346
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