N,N'-Dimethylethylenediamine

N,N'-Dimethylethylenediamine
Names
	Preferred IUPAC name N,N′-Dimethylethane-1,2-diamine
	Other names N,N′-Dimethyl-1,2-ethanediamine
Identifiers
CAS Number	110-70-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	7779;
ECHA InfoCard	100.003.450
EC Number	203-793-3;
PubChem CID	8070;
UNII	JBC5EX42TL ;
CompTox Dashboard (EPA)	DTXSID4058730 ;
	InChI InChI=1S/C4H12N2/c1-5-3-4-6-2/h5-6H,3-4H2,1-2H3 Key: KVKFRMCSXWQSNT-UHFFFAOYSA-N;
	SMILES CNCCNC;
Properties
Chemical formula	C4H12N2
Molar mass	88.154 g·mol−1
Appearance	Colorless liquid
Density	0.819 g/mL
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

N,N'-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. 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:

O=CRR' + C₂H₄[NH(CH₃)]₂ → C₂H₄[NH(CH₃)]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

DMEDA complexes of copper(I) halides are used to catalyze C-N coupling reactions.^[4]

References

^ 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
^ 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.
^ 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.
^ Krout, M. R.; Mohr, J. T.; Stoltz, B. M. (2009). "PREPARATION OF (S)-tert-ButylPHOX". Organic Syntheses. 86: 181. doi:10.15227/orgsyn.086.0181. PMC 2805096. PMID 20072718.

[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.

[4] Krout, M. R.; Mohr, J. T.; Stoltz, B. M. (2009). "PREPARATION OF (S)-tert-ButylPHOX". Organic Syntheses. 86: 181. doi:10.15227/orgsyn.086.0181. PMC 2805096. PMID 20072718.

[1]

[2]

[3]

[4]

Reactions

See also

References