Bis(dimethylamino)methane
Bis(dimethylamino)methane is the organic compound with the formula [(CH3)2N]2CH2. It is classified as an aminal as well as a ditertiary amine, in fact the simplest. It is a colorless liquid that is widely available. It is prepared by the reaction of dimethylamine and formaldehyde:[1]
- 2 (CH3)2NH + CH2O → [(CH3)2N]2CH2 + H2O
 | |
| Names | |
|---|---|
| Other names
N,N,N',N'-tetramethylmethylenediamine | |
| Identifiers | |
3D model (JSmol) |
|
| ChemSpider | |
| ECHA InfoCard | 100.000.114 |
| EC Number |
|
PubChem CID |
|
| UNII | |
| UN number | 1993 |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C5H14N2 | |
| Molar mass | 102.181 g·mol−1 |
| Appearance | colorless liquid |
| Density | 0.749 g/cm3 |
| Melting point | −12 °C (10 °F; 261 K) |
| Boiling point | 85 °C (185 °F; 358 K) |
| Hazards | |
| GHS labelling: | |
  | |
| Danger | |
| H225, H314 | |
| P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
It is used for the dimethylaminomethylation reactions, the reaction being initiated by the addition of a strong, anhydrous acid:[2]
- [(CH3)2N]2CH2 + H+ → (CH3)2NCH2+ + (CH3)2NH
Related reagents
- N,N,N′,N′-Tetramethylformamidinium chloride
- Eschenmoser's salt is used for similar applications.
References
- Gaudry, Michel; Jasor, Yves; Khac, Trung Bui (1979). "Regioselective Mannich Condensation with Dimethyl(Methylene)ammonium Trifluoroacetate: 1-(Dimethylamino)-4-methyl-3-pentanone". Org. Synth. 59: 153. doi:10.15227/orgsyn.059.0153.
- Allen J. Duplantier. "Bis(dimethylamino)methane". eEROS, Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rb143.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.