Eschenmoser's salt

Eschenmoser's salt

Names
IUPAC name Dimethylmethylideneammonium iodide
Identifiers
CAS Number	33797-51-2 (Iodide) 30354-18-8 (Chloride)
3D model (Jmol)	Interactive image Interactive image
ChemSpider	2006292 Y
ECHA InfoCard	100.046.968
PubChem	2724133
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
SMILES C[N+](C)=C.[I-] [I-].[N+](=C)(C)C
Properties
Chemical formula	C3H8NI
Molar mass	185.01 g/mol
Appearance	colorless hygroscopic crystals
Melting point	116 °C (241 °F; 389 K)
Solubility in water	decomposes
Hazards
R-phrases	R36/37/38
S-phrases	S26 S36
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
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], after Horst Böhme) and trifluoroacetate, have similar properities and applications.^[1]

References