Bis(dimethylamino)methane

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

Bis(dimethylamino)methane

Names
Other names N,N,N',N'-tetramethylmethylenediamine
Identifiers
CAS Number	51-80-9
3D model (JSmol)	Interactive image
ChemSpider	5624
ECHA InfoCard	100.000.114
EC Number	200-124-7
PubChem CID	5829
UNII	Z870I525KS
UN number	1993
CompTox Dashboard (EPA)	DTXSID1058761
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 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 [77 °F], 100 kPa). Infobox references

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]

Related reagents

• N,N,N′,N′-Tetramethylformamidinium chloride
• Eschenmoser's salt is used for similar applications.

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.