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D157805

Sigma-Aldrich

N,N′-Dimethylethylenediamine

98%

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Synonym(s):
DMEDA, 1,2-Bis(methylamino)ethane
Linear Formula:
CH3NHCH2CH2NHCH3
CAS Number:
Molecular Weight:
88.15
Beilstein/REAXYS Number:
878142
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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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1 of 4

This Item
T22500T7024411019
N,N′-Dimethylethylenediamine 98%

D157805

N,N′-Dimethylethylenediamine

-
N,N,N′,N′-Tetramethylethylenediamine BioReagent, for molecular biology, ≥99% (GC)

T7024

N,N,N′,N′-Tetramethylethylenediamine

Essential+ Grade
Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

refractive index

n20/D 1.431 (lit.)

refractive index

n20/D 1.4179 (lit.)

refractive index

n20/D 1.4179 (lit.)

refractive index

n20/D 1.4179 (lit.)

bp

119 °C (lit.)

bp

120-122 °C (lit.)

bp

120-122 °C (lit.)

bp

120-122 °C (lit.)

form

liquid

form

-

form

-

form

liquid

density

0.819 g/mL at 20 °C (lit.)

density

0.775 g/mL at 20 °C (lit.)

density

0.775 g/mL at 20 °C (lit.)

density

0.775 g/mL at 20 °C (lit.)

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.

pictograms

FlameCorrosion

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

78.8 °F - closed cup

flash_point_c

26 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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An environmentally benign procedure for the Cu-catalyzed cyanation of aryl bromides.
Schareina T, et al.
Tetrahedron Letters, 46(15), 2585-2588 (2005)
Iron?Catalyzed C N Cross?Coupling of Sulfoximines with Aryl Iodides.
Correa A, et al.
Advanced Synthesis & Catalysis, 350(3), 391-394 (2008)
Organocatalysis in cross-coupling: DMEDA-catalyzed direct C? H arylation of unactivated benzene.
Liu W, et al.
Journal of the American Chemical Society, 132(47), 16737-16740 (2010)
Copper-catalyzed synthesis of N-fused heterocycles through regioselective 1, 2-aminothiolation of 1, 1-dibromoalkenes.
Xu H, et al.
Organic Letters, 12(16), 3704-3707 (2010)
Generation of benzoimidazo [1, 5-a] imidazoles via a copper-catalyzed tandem reaction of carbodiimide and isocyanoacetate.
Qiu G, et al.
Chemical Communications (Cambridge, England), 48(48), 6046-6048 (2012)

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