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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:
110-70-3
Molecular Weight:
88.15
Beilstein:
878142
EC Number:
203-793-3
MDL number:
MFCD00008290
UNSPSC Code:
12352100
PubChem Substance ID:
24893484
NACRES:
NA.22

Quality Level

200

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
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H226,H314

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)

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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)
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)
Kim A Lennox et al.
Oligonucleotides, 16(1), 26-42 (2006-04-06)
A wide variety of modified oligonucleotides have been tested as antisense agents. Each chemical modification produces a distinct profile of potency, toxicity, and specificity. Novel cationic phosphoramidate-modified antisense oligonucleotides have been developed recently that have unique and interesting properties. We
Ghotas Evindar et al.
The Journal of organic chemistry, 71(5), 1802-1808 (2006-02-25)
A general method for the formation of benzoxazoles via a copper-catalyzed cyclization of ortho-haloanilides is reported. This approach complements the more commonly used strategies for benzoxazole formation which require 2-aminophenols as substrates. The reaction involves an intramolecular C-O cross-coupling of
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