Eschenmoser's salt
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| Eschenmoser's salt | |
|---|---|
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| General | |
| Systematic name | Dimethylmethylideneammonium iodide |
| Molecular formula | C3H8NI |
| SMILES | C[N+](C)=C.[I-] |
| Molar mass | 185.01 g/mol |
| Appearance | colorless hygroscopic crystals |
| CAS number | [30354-18-8] (Chloride) [33797-51-2] (Iodide) |
| Properties | |
| Solubility in water | decomp. |
| solubility in other solvents | DMF, slightly in THF |
| Melting point | 116 °C |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | ? |
| NFPA 704 | |
| Flash point | ? °C |
| R/S statement | R: 36/37/38 S: 26-36 |
| RTECS number | ? |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related compounds | ? |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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.
[edit] References
- E. F. Kleinman in "Dimethylmethyleneammonium Iodide and Chloride" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York.
- H. Böhme, E. Mundlos, O.-E.Herboth, "Über Darstellung und Eigenschaften alpha-Halogenierter Amine" Chemische Berichte 1957, 90, 2003-2008.
[edit] External links
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