Chemistry:Bis(dimethylamino)methane
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Names | |
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Other names
N,N,N',N'-tetramethylmethylenediamine
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
EC Number |
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PubChem CID
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UNII | |
UN number | 1993 |
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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 pictograms | ![]() ![]() |
GHS Signal word | Danger |
H225, H314 | |
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P363, P370+378, P403+235, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
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
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 (2001). "Bis(dimethylamino)methane". EEROS, Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rb143. ISBN 0471936235.
![]() | Original source: https://en.wikipedia.org/wiki/Bis(dimethylamino)methane.
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