Eschenmoser's salt

Eschenmoser's salt

Names
IUPAC name Dimethylmethylideneammonium iodide
Identifiers
CAS Number	33797-51-2 (Iodide) Y 30354-18-8 (Chloride) N
3D model (JSmol)	Interactive image Interactive image
ChemSpider	2006292 Y
ECHA InfoCard	100.046.968
PubChem CID	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R-phrases (outdated)	R36/37/38
S-phrases (outdated)	S26 S36
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (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.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.

Analogous salts, dimethylmethylideneammonium chloride (Böhme's salt, after Horst Böhme) and trifluoroacetate, have similar properities and applications.