1,2-Dimethylethylenediamine

1,2-Dimethylethylenediamine (DMEDA) is the organic compound with the formula (CH3NH)2C2H4. It is a colorless liquid with a fishy odor. It features two secondary amine functional groups.

1,2-Dimethylethylenediamine
Names
Preferred IUPAC name
N,N′-Dimethylethane-1,2-diamine
Other names
N,N′-Dimethyl-1,2-ethanediamine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.450
UNII
  • InChI=1S/C4H12N2/c1-5-3-4-6-2/h5-6H,3-4H2,1-2H3
    Key: KVKFRMCSXWQSNT-UHFFFAOYSA-N
  • CNCCNC
Properties
C4H12N2
Molar mass 88.154 g·mol−1
Appearance Colorless liquid
Boiling point 120 °C (248 °F; 393 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Reactions

DMEDA is used as a chelating diamine for the preparation of metal complexes, some of which function as homogeneous catalysts.[1][2]

The compound is used as a precursor to imidazolidines by condensation with ketones or with aldehydes:

RR'CO + C2H4(CH3NH)2 → C2H4(CH3N)2CRR' + H2O
View down chelate ring-Ni axis in trans-[NiCl2(DMEDA)2] (one DMEDA and chloride ligands omitted for clarity).[3] Color code: green = Ni, violet = N, dark gray = C

See also

References
  1. Chan, Timothy R.; Hilgraf, Robert; Sharpless, K. Barry; Fokin, Valery V. "Polytriazoles as copper(I)-stabilizing ligands in catalysis" Organic Letters 2004, volume 6, 2853-2855. doi:10.1021/ol0493094
  2. Klapars, Artis; Huang, Xiaohua; Buchwald, Stephen L. (2002). "A General and Efficient Copper Catalyst for the Amidation of Aryl Halides". Journal of the American Chemical Society. 124 (25): 7421–7428. doi:10.1021/ja0260465. PMID 12071751.
  3. Ariyananda, W. G. Piyal; Norman, Richard E. (2006). "trans-Dichlorobis(N,N'-dimethylethane-1,2-diamine-κ2N,N')nickel(II)". Acta Crystallographica Section E. 62: m2339–m2341. doi:10.1107/S1600536806033770.
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