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674613

Sigma-Aldrich

Tetrakis(dimethylamino)ethylene

Synonym(s):

Octamethylethylenetetramine, TDAE

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About This Item

Linear Formula:
[(CH3)2N]2C=C[N(CH3)2]2
CAS Number:
996-70-3
Molecular Weight:
200.32
Beilstein/REAXYS Number:
1705900
EC Number:
213-638-1
MDL number:
MFCD00009601
UNSPSC Code:
12352116
PubChem Substance ID:
24885226
NACRES:
NA.22

Quality Level

100

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.48 (lit.)

bp

59 °C/0.9 mmHg (lit.)

density

0.861 g/mL at 25 °C (lit.)

functional group

amine

SMILES string

CN(C)\C(N(C)C)=C(\N(C)C)N(C)C

InChI

1S/C10H24N4/c1-11(2)9(12(3)4)10(13(5)6)14(7)8/h1-8H3

InChI key

CBXRMKZFYQISIV-UHFFFAOYSA-N

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Application

Involved in TDAE methodology for coupling and intramolecular Buchwald reactions

Acts as a reducing agent

Reactant involved in:
  • Dioxygenation
  • Insertion of aluminum anion into the C-N bond
  • Chemiluminescent reactions with oxygen
Reagent used to convert α-bromoketones into 1,4-diketones.

pictograms

FlameCorrosion
GHS02,GHS05

signalword

Danger

hcodes

H226,H314

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

127.4 °F - closed cup

flash_point_c

53 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT7378
MKCV4709
MKCQ3704
MKCR5610
MKCQ7627

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Patrick Weis et al.
Physical chemistry chemical physics : PCCP, 21(35), 18877-18892 (2019-08-23)
We present high-resolution trapped ion mobility spectrometry (TIMS) measurements for fullerene ions in molecular nitrogen. Three different charge states were studied (monocations, monoanions and dianions) with fullerenes ranging in size from C60 to C150. Ions were prepared by either electrospray
Tetrahedron Letters, 47, 5565-5565 (2006)
Kyungwho Choi et al.
ACS applied materials & interfaces, 10(28), 23891-23899 (2018-06-28)
Thermoelectric (TE) energy conversion with nontraditional organic materials is promising in wearable electronics and roll-to-roll manufacturing because of mechanical flexibility, lightweight, and easy processing. Although typical organic materials have a benefit of low thermal conductivity that creates a large temperature
Wen-Bin Luo et al.
Advanced materials (Deerfield Beach, Fla.), 27(43), 6862-6869 (2015-09-25)
Porous AgPd-Pd composite nanotubes (NTs) are used as an efficient bifunctional catalyst for the oxygen reduction and evolution reactions in lithium-oxygen batteries. The porous NT structure can facilitate rapid O2 and electrolyte diffusion through the NTs and provide abundant catalytic
Hong Wang et al.
Advanced materials (Deerfield Beach, Fla.), 27(43), 6855-6861 (2015-10-02)
Hybrids of carbon nanotubes (CNTs) and poly(3,4-ethylenedioxythiophene) (PEDOT) treated by tetrakis(dimethylamino)ethylene (TDAE) have large n-type voltages in response to temperature differences. The reduced carrier concentration by TDAE reduction and partially percolated CNT networks embedded in the PEDOT matrix result in
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Articles

Tetrakis(dimethylamino)ethylene (TDAE)

In 2001, Professor William Dolbier, Jr., at the University of Florida reported1 an approach to nucleophilic trifluoromethylation based on the generation of a trifluoromethyl anion using CF3I in the presence of a powerful twoelectron reductant, tetrakis(dimethylamino)ethylene (TDAE)

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