Eschenmoser's salt

Eschenmoser's salt
IUPAC name

Dimethylmethylideneammonium iodide
Identifiers
CAS number 33797-51-2, 
(Iodide)[30354-18-8] (Chloride)
PubChem 2724133
ChemSpider 2006292 Y
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C3H8NI
Molar mass 185.01 g/mol
Appearance colorless hygroscopic crystals
Melting point

116 °C, 389 K, 241 °F
Solubility in water decomp.
Hazards
R-phrases R36/37/38
S-phrases S26 S36
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 after whom the reagent is named.[3]

References

  1. ^ E. F. Kleinman in "Dimethylmethyleneammonium Iodide and Chloride" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York.
  2. ^ H. Böhme, E. Mundlos, O.-E.Herboth, "Über Darstellung und Eigenschaften alpha-Halogenierter Amine" Chemische Berichte 1957, 90, 2003-2008.
  3. ^ 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.