Eschenmoser's salt

In organic chemistry, Eschenmoser's salt (named for Albert Eschenmoser) is the ionic, organic compound [(CH3)2NCH2]I. It is the iodide salt of the dimethylaminomethylene cation [(CH3)2NCH2]+.

Eschenmoser's salt
Names
Preferred IUPAC name
N,N-Dimethylmethaniminium iodide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.046.968
PubChem CID
UNII
  • 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
C3H8NI
Molar mass 185.01 g/mol
Appearance colorless hygroscopic crystals
Melting point 116 °C (241 °F; 389 K)
decomposes
Hazards
GHS labelling:
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
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

The dimethylaminomethylene cation is a strong dimethylaminomethylating agent, used to prepare derivatives of the type RCH2N(CH3)2. Enolates, silyl enol ethers, 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.

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