Bis(dimethylamino)methane explained
Bis(dimethylamino)methane is the organic compound with the formula [(CH<sub>3</sub>)<sub>2</sub>N]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 → [(CH<sub>3</sub>)<sub>2</sub>N]2CH2 + H2O
It is used for the dimethylaminomethylation reactions, the reaction being initiated by the addition of a strong, anhydrous acid:[2]
[(CH<sub>3</sub>)<sub>2</sub>N]2CH2 + H+ → (CH3)2NCH2+ + (CH3)2NH
Bis(dimethylamino)methane, being a Lewis base, functions as a bidentate ligand.[3]
Related reagents
References
- 10.15227/orgsyn.059.0153. Regioselective Mannich Condensation with Dimethyl(Methylene)ammonium Trifluoroacetate: 1-(Dimethylamino)-4-methyl-3-pentanone. Michel. Gaudry. Yves. Jasor. Trung Bui . Khac. Org. Synth.. 1979. 59. 153.
- E-EROS Encyclopedia of Reagents for Organic Synthesis. Bis(dimethylamino)methane. 10.1002/047084289X.rb143. Allen J. Duplantier. 2001. 0471936235.
- 10.1002/chem.201600810 . Siloxymethylamines as Aminomethylation Reagents for Amines Leading to Labile Diaminomethanes That Can Be Trapped as Their [Mo(CO)4] Complexes . 2016 . Sharma . Hemant K. . Gonzalez . Paulina E. . Craig . Alexander L. . Chakrabarty . Sanchita . Metta-Magaña . Alejandro . Pannell . Keith H. . Chemistry – A European Journal . 22 . 22 . 7363–7366 . 27111263 .
