Eschenmoser's salt

Eschenmoser's salt

Names
IUPAC name Dimethyl(methylidene)ammonium 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
UNII	5C42I004S1 Y
CompTox Dashboard (EPA)	DTXSID10369115
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Eschenmoser's salt, dimethyl(methylidene)ammonium 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 methylidenated ketones. The salt was first prepared by the group of Albert Eschenmoser after whom the reagent is named.

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

See also

• Vilsmeier reagent, [(CH₃)₂NCHCl]Cl