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
SMILES C[N+](C)=C.[I-] [I-].[N+](=C)(C)C
InChI InChI=1S/C3H8N.HI/c1-4(2)3;/h1H2,2-3H3;1H/q+1;/p-1 Y Key: VVDUZZGYBOWDSQ-UHFFFAOYSA-M Y InChI=1/C3H8N.HI/c1-4(2)3;/h1H2,2-3H3;1H/q+1;/p-1 Key: VVDUZZGYBOWDSQ-REWHXWOFAW
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.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.