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| Names | |
|---|---|
| Preferred IUPAC name 1-Chloro-N,N-dimethylmethaniminium chloride | |
| Other names (chloromethylene)dimethyliminium chloride | |
| Identifiers | |
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3D model (JSmol) | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.102.443 |
| EC Number |
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| UNII | |
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| Properties | |
| C3H7Cl2N | |
| Molar mass | 128.00 g·mol−1 |
| Appearance | white solid |
| Melting point | 132 °C (270 °F; 405 K) |
| Hazards | |
| GHS labelling: | |
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| Danger | |
| H290,H302,H314,H360 | |
| P201,P202,P234,P260,P264,P270,P280,P281,P301+P312,P301+P330+P331,P303+P361+P353,P304+P340,P305+P351+P338,P308+P313,P310,P321,P330,P363,P390,P404,P405,P501 | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
TheVilsmeier reagent is anorganic compound with the formula [(CH3)2NCHCl]Cl. It is a salt consisting of the N,N-dimethyliminium cation ([(CH3)2N=CHCl]+) and chloride anion. Depending on the particular reaction, the anion can vary. In typical POCl3-based reactions, the anion is PO2Cl2−. Theiminium cation [(CH3)2N=CHCl]+ is the reactive component of interest. This iminium species is a derivative of theimidoyl chloride CH3N=CHCl. Analogues of this particular reagent are generated when tertiary amides other than DMF are treated with POCl3.
The salt is a white solid that is soluble in polar organic solvents. Vilsmeier reagent is the active intermediate in the formylation reactions, theVilsmeier reaction or Vilsmeier-Haack reaction that use mixtures ofdimethylformamide andphosphorus oxychloride to generate the Vilsmeier reagent, which in turn attacks a nucleophilic substrate and eventually hydrolyzes to give formyl. It is a source of "O=CH+".[1]
