Names | |
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Other names N,N,N',N'-tetramethylmethylenediamine | |
Identifiers | |
CAS Number | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.000.114 |
EC Number |
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PubChem CID | |
UNII | |
UN number | 1993 |
CompTox Dashboard (EPA) | |
InChI
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SMILES
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Properties | |
Chemical formula | C5H14N2 |
Molar mass | 102.181 g·mol |
Appearance | colorless liquid |
Density | 0.749 g/cm |
Melting point | −12 °C (10 °F; 261 K) |
Boiling point | 85 °C (185 °F; 358 K) |
Hazards | |
GHS labelling: | |
Pictograms | |
Signal word | Danger |
Hazard statements | H225, H314 |
Precautionary statements | 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 , 100 kPa). Infobox references |
Bis(dimethylamino)methane is the organic compound with the formula 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:
- 2 (CH3)2NH + CH2O → 2CH2 + H2O
It is used for the dimethylaminomethylation reactions, the reaction being initiated by the addition of a strong, anhydrous acid:
- 2CH2 + H → (CH3)2NCH2 + (CH3)2NH
Bis(dimethylamino)methane, being a Lewis base, functions as a bidentate ligand.
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". 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.