N,N'-Dimethylethylenediamine
{{Chembox
| ImageFile = 1,2-C2H4(NHMe)2.png
| PIN = N,N{{prime}}-Dimethylethane-1,2-diamine
| OtherNames = N,N{{prime}}-Dimethyl-1,2-ethanediamine
|Section1={{Chembox Identifiers
| CASNo = 110-70-3
| CASNo_Ref = {{Cascite|correct|CAS}}
| ChemSpiderID = 7779
| EC_number = 203-793-3
| PubChem = 8070
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = JBC5EX42TL
| StdInChI = 1S/C4H12N2/c1-5-3-4-6-2/h5-6H,3-4H2,1-2H3
| StdInChIKey = KVKFRMCSXWQSNT-UHFFFAOYSA-N
| SMILES = CNCCNC
}}
|Section2={{Chembox Properties
| C=4|H=12|N=2
| Appearance = Colorless liquid
| BoilingPtC = 120
| Density = 0.819 g/mL
}}
}}
N,N'-Dimethylethylenediamine (DMEDA) is the organic compound with the formula (CH{{sub|3}}NH){{sub|2}}C{{sub|2}}H{{sub|4}}. 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.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}}{{cite journal|title=A General and Efficient Copper Catalyst for the Amidation of Aryl Halides|last1=Klapars|first1=Artis|last2=Huang|first2=Xiaohua|last3=Buchwald|first3=Stephen L.|journal=Journal of the American Chemical Society|year=2002|volume=124|issue=25|pages=7421–7428|doi=10.1021/ja0260465|pmid=12071751}}
The compound is used as a precursor to imidazolidines by condensation with ketones or with aldehydes:
:{{chem2|O\dCRR' + C2H4[NH(CH3)]2 → C2H4[NH(CH3)]2CRR' + H2O}}
DMEDA complexes of copper(I) halides are used to catalyze C-N coupling reactions.{{cite journal |doi=10.15227/orgsyn.086.0181 |title=PREPARATION OF (S)-tert-ButylPHOX |journal=Organic Syntheses |date=2009 |volume=86 |page=181 |pmid=20072718 |last1=Krout |first1=M. R. |last2=Mohr |first2=J. T. |last3=Stoltz |first3=B. M. |pmc=2805096 }}
See also
References
{{Reflist}}
{{DEFAULTSORT:Dimethylethylenediamine, 1, 2-}}