N,N'-Dimethylethylenediamine Explained

N,N'-Dimethylethylenediamine (DMEDA) is the organic compound with the formula (CHNH)CH. It is a colorless liquid with a fishy odor. It features two secondary amine functional groups. Regarding its name, N and N' indicate that the methyl groups are attached to different nitrogen atoms.

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:

DMEDA complexes of copper(I) halides are used to catalyze C-N coupling reactions.^[3]

See also

• 1,1-Dimethylethylenediamine
• Dimethylaminopropylamine

Notes and 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.
2. A General and Efficient Copper Catalyst for the Amidation of Aryl Halides. Klapars. Artis. Huang. Xiaohua. Buchwald. Stephen L.. Journal of the American Chemical Society. 2002. 124. 25. 7421–7428. 10.1021/ja0260465. 12071751.
3. 10.15227/orgsyn.086.0181 . PREPARATION OF (S)-tert-ButylPHOX . Organic Syntheses . 2009 . 86 . 181 . 20072718 . Krout . M. R. . Mohr . J. T. . Stoltz . B. M. . 2805096 .