D157805
N,N′-Dimethylethylenediamine
98%
Synonym(s):
DMEDA, 1,2-Bis(methylamino)ethane
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About This Item
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Quality Level
Assay
98%
form
liquid
refractive index
n20/D 1.431 (lit.)
bp
119 °C (lit.)
density
0.819 g/mL at 20 °C (lit.)
SMILES string
CNCCNC
InChI
1S/C4H12N2/c1-5-3-4-6-2/h5-6H,3-4H2,1-2H3
InChI key
KVKFRMCSXWQSNT-UHFFFAOYSA-N
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Application
N,N′-Dimethylethylenediamine can be used as a ligand in the following processes:
- Copper-catalyzed cyanations of aryl bromides using potassium hexacyanoferrate(II) to form the corresponding benzonitriles.
- Copper-catalyzed tandem reaction of carbodiimide and isocyanoacetate to form benzoimidazo[1,5-α]imidazoles.
- Aminothiolation of 1,1-dibromoalkene to form N-fused heterocycles.
- In combination with ferrous chloride, for the N-arylation of NH-sulfoximines with aryl iodides to form N-arylsulfoximines.
- It can catalyze the direct C-H arylation of unactivated benzene in the presence of potassium tert-butoxide to form the corresponding biaryl.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
78.8 °F - closed cup
Flash Point(C)
26 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Organocatalysis in cross-coupling: DMEDA-catalyzed direct C? H arylation of unactivated benzene.
Journal of the American Chemical Society, 132(47), 16737-16740 (2010)
Iron?Catalyzed C N Cross?Coupling of Sulfoximines with Aryl Iodides.
Advanced Synthesis & Catalysis, 350(3), 391-394 (2008)
Copper-catalyzed synthesis of N-fused heterocycles through regioselective 1, 2-aminothiolation of 1, 1-dibromoalkenes.
Organic Letters, 12(16), 3704-3707 (2010)
An environmentally benign procedure for the Cu-catalyzed cyanation of aryl bromides.
Tetrahedron Letters, 46(15), 2585-2588 (2005)
Generation of benzoimidazo [1, 5-a] imidazoles via a copper-catalyzed tandem reaction of carbodiimide and isocyanoacetate.
Chemical Communications (Cambridge, England), 48(48), 6046-6048 (2012)
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