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D157805

Sigma-Aldrich

N,N′-Dimethylethylenediamine

98%

Synonym(s):

DMEDA, 1,2-Bis(methylamino)ethane

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About This Item

Linear Formula:
CH3NHCH2CH2NHCH3
CAS Number:
Molecular Weight:
88.15
Beilstein:
878142
EC Number:
MDL number:
UNSPSC Code:
12352100
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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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

Signal Word

Danger

Hazard 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Iron?Catalyzed C N Cross?Coupling of Sulfoximines with Aryl Iodides.
Correa A, et al.
Advanced Synthesis & Catalysis, 350(3), 391-394 (2008)
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)
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)
An environmentally benign procedure for the Cu-catalyzed cyanation of aryl bromides.
Schareina T, et al.
Tetrahedron Letters, 46(15), 2585-2588 (2005)
Chandi C Malakar et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(29), 8882-8885 (2012-06-26)
Water makes it possible: The Cu(2)O-catalyzed reaction between easily available o-bromobenzylbromides and benzamidines by using Cs(2)CO(3) as the base and N,N'-dimethylethylenediamine (DMEDA) as the additive in water as the solvent gives access to substituted quinazolines in a single step with

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