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127078

Sigma-Aldrich

N,N,N′,N′-Tetraethylethylenediamine

98%

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Synonym(s):
TEEDA
Linear Formula:
(C2H5)2NCH2CH2N(C2H5)2
CAS Number:
Molecular Weight:
172.31
EC Number:
MDL number:
PubChem Substance ID:

Assay

98%

form

liquid

refractive index

n20/D 1.4343 (lit.)

bp

189-192 °C (lit.)

density

0.808 g/mL at 25 °C (lit.)

SMILES string

CCN(CC)CCN(CC)CC

InChI

1S/C10H24N2/c1-5-11(6-2)9-10-12(7-3)8-4/h5-10H2,1-4H3

InChI key

DIHKMUNUGQVFES-UHFFFAOYSA-N

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1 of 4

This Item
T22500T7024411019
N,N,N′,N′-Tetramethylethylenediamine BioReagent, for molecular biology, ≥99% (GC)

Sigma-Aldrich

T7024

N,N,N′,N′-Tetramethylethylenediamine

Essential+ Grade
form

liquid

form

-

form

-

form

liquid

refractive index

n20/D 1.4343 (lit.)

refractive index

n20/D 1.4179 (lit.)

refractive index

n20/D 1.4179 (lit.)

refractive index

n20/D 1.4179 (lit.)

bp

189-192 °C (lit.)

bp

120-122 °C (lit.)

bp

120-122 °C (lit.)

bp

120-122 °C (lit.)

density

0.808 g/mL at 25 °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, N′,N′-Tetraethylethylenediamine (TEEDA) has been used in the synthesis of amine ligands using simple or double intramolecular dealkylation reaction. TEEDA exhibits selective β-lithiation during deprotonation with lithiumalkyls.

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Inhalation

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

138.2 °F - closed cup

Flash Point(C)

59 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Viktoria H Gessner et al.
Journal of the American Chemical Society, 130(44), 14412-14413 (2008-10-10)
TMEDA and its ethyl-substituted analogue, TEEDA, show a different behavior toward the deprotonation with lithiumalkyls. While TMEDA mainly undergoes alpha-lithiation of its methyl group, TEEDA shows selective beta-lithiation with following elimination of ethene. The crystal structure of the monomeric intermediate
M Esther Morilla et al.
Chemical communications (Cambridge, England), (17)(17), 1848-1849 (2002-09-26)
N,N, N',N'-Tetraethylethylenediamine undergoes simple or double intramolecular dealkylation reactions in the presence of the complexes [RuCl2(diene)]n (diene = cod, nbd) or trans-[RuCl2(diene)(morfoline)2 at 80 degrees C to afford chelating amine ligands which contains one or two N-H functionalities.
Wei Xiao et al.
Biochimica et biophysica acta. General subjects, 1862(8), 1760-1769 (2018-05-12)
The inorganic core of the iron storage protein, ferritin, is recognized as being analogous to the poorly crystalline iron mineral, ferrihydrite (Fh). Fh is also abundant in soils where it is central to the redox cycling of particular soil contaminants
Lan-Fang Hu et al.
Molecules (Basel, Switzerland), 25(2) (2020-01-16)
The copolymerization of biorenewable succinic anhydride (SA) with propylene oxide (PO) is a promising way to synthesize biodegradable aliphatic polyesters. However, the catalytic systems for this reaction still deserve to be explored because the catalytic activity of the reported catalysts

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