Bis(dimethylamino)methane

Bis(dimethylamino)methane
Names
IUPAC name
N,N,N′,N′-Tetramethylmethanediamine
Other names
N,N,N′,N′-Tetramethylmethylenediamine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.114
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:
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).
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:

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:

[(CH3)2N]2CH2 + H+ → (CH3)2NCH2+ + (CH3)2NH

Bis(dimethylamino)methane, being a Lewis base, functions as a bidentate ligand.

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