French
DeutschBis(dimethylamino)methane
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| Names | |
|---|---|
| Other names N,N,N',N'-tetramethylmethylenediamine | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.000.114 |
| EC Number |
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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). | |
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
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
Bis(dimethylamino)methane, being a Lewis base, functions as a bidentate ligand.[3]
Related reagents
[edit]- N,N,N′,N′-Tetramethylformamidinium chloride
- Eschenmoser's salt is used for similar applications.
References
[edit]- ^ 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 (2001). "Bis(dimethylamino)methane". E-EROS, Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rb143. ISBN 0471936235.
- ^ Sharma, Hemant K.; Gonzalez, Paulina E.; Craig, Alexander L.; Chakrabarty, Sanchita; Metta-Magaña, Alejandro; Pannell, Keith H. (2016). "Siloxymethylamines as Aminomethylation Reagents for Amines Leading to Labile Diaminomethanes That Can Be Trapped as Their [Mo(CO)4] Complexes". Chemistry – A European Journal. 22 (22): 7363–7366. doi:10.1002/chem.201600810. PMID 27111263.