N,N'-Dimethylethylenediamine
Chemical compound
From Wikipedia, the free encyclopedia
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.
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| Names | |
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| Preferred IUPAC name
N,N′-Dimethylethane-1,2-diamine | |
| Other names
N,N′-Dimethyl-1,2-ethanediamine | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.003.450 |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| 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).
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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
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DMEDA complexes of copper(I) halides are used to catalyze C-N coupling reactions.[4]