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

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". EEROS, Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rb143. ISBN 0471936235.

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*[CID]: Compound ID
*[H225]: Highly flammable liquid and vapour
*[H314]: Causes severe skin burns and eye damage
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P233]: Keep container tightly closed
*[P240]: Ground/bond container and receiving equipment
*[P241]: Use explosion-proof electrical/ventilating/light/…/equipment
*[P242]: Use only non-sparking tools
*[P243]: Take precautionary measures against static discharge
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P301+330+331]: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P310]: Immediately call a POISON CENTER or doctor/physician
*[P321]: Specific treatment (see … on this label)
*[P363]: Wash contaminated clothing before reuse
*[P370+378]: In case of fire: Use … for extinction
*[P403+235]: Store in a well ventilated place. Keep cool
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …