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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:
150-77-6
Molecular Weight:
172.31
EC Number:
205-770-3
MDL number:
MFCD00009055
UNSPSC Code:
12352100
PubChem Substance ID:
24847759
NACRES:
NA.22

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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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

H226,H302 + H332,H314

Hazard Classifications

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

WGK

WGK 1

Flash Point(F)

138.2 °F

Flash Point(C)

59 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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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.
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
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

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