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Eschenmoser's salt



Eschenmoser's salt
IUPAC name Dimethylmethylideneammonium iodide
Identifiers
CAS number [30354-18-8] (Chloride)
[33797-51-2] (Iodide)
SMILES C[N+](C)=C.[I-]
Properties
Molecular formula C3H8NI
Molar mass 185.01 g/mol
Appearance colorless hygroscopic crystals
Melting point

116 °C

Solubility in water decomp.
Hazards
R-phrases 36/37/38
S-phrases 26-36
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Eschenmoser's salt, dimethylmethylideneammonium iodide, is a strong dimethylaminomethylating agent, used to prepare derivatives of the type RCH2N(CH3)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 after whom the reagent is named.[1]

References

  • E. F. Kleinman in "Dimethylmethyleneammonium Iodide and Chloride" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York.
  • H. Böhme, E. Mundlos, O.-E.Herboth, "Über Darstellung und Eigenschaften alpha-Halogenierter Amine" Chemische Berichte 1957, 90, 2003-2008.
  1. ^ Jakob Schreiber, Hans Maag, Naoto Hashimoto, Albert Eschenmoser (1971). "Dimethyl(methylene)ammonium Iodide". Angewandte Chemie International Edition in English 10 (5): 330-331. doi:10.1002/anie.197103301.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Eschenmoser's_salt". A list of authors is available in Wikipedia.
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