Bis(dimethylamino)methane

Bis(dimethylamino)methane
Names
Other names
N,N,N',N'-tetramethylmethylenediamine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.114 Edit this at Wikidata
EC Number
  • 200-124-7
UNII
UN number 1993
  • InChI=1S/C5H14N2/c1-6(2)5-7(3)4/h5H2,1-4H3
    Key: VGIVLIHKENZQHQ-UHFFFAOYSA-N
  • CN(C)CN(C)C
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:
GHS02: FlammableGHS05: Corrosive
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]

References

  1. ^ 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.
  2. ^ Allen J. Duplantier (2001). "Bis(dimethylamino)methane". E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rb143. ISBN 0471936235.
  3. ^ 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.