Bis(Dimethylamino)Methane

Bis(dimethylamino)methane
Names
	Other names N,N,N',N'-tetramethylmethylenediamine
Identifiers
CAS Number	51-80-9;
3D model (JSmol)	Interactive image;
ChemSpider	5624;
EC Number	200-124-7;
PubChem CID	5829;
UNII	Z870I525KS;
UN number	1993
	InChI InChI=1S/C5H14N2/c1-6(2)5-7(3)4/h5H2,1-4H3 Key: VGIVLIHKENZQHQ-UHFFFAOYSA-N;
	SMILES CN(C)CN(C)C;
Properties
Chemical formula	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
GHS hazard statements	H225, H314
GHS precautionary statements	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. "Bis(dimethylamino)methane". eEROS, Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rb143.

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[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. "Bis(dimethylamino)methane". eEROS, Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rb143.