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Merck
CN

674613

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:
1705900
EC Number:
213-638-1
MDL number:
MFCD00009601
UNSPSC Code:
12352116
PubChem Substance ID:
24885226
NACRES:
NA.22

Key Documents

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Assay

≥85.0%

Quality Level

100

form

liquid

reaction suitability

reaction type: C-C Bond Formation

refractive index

n/D 1.48 ((lit.))
n20/D 1.48 (lit.)

bp

59 °C ((lit.))
59 °C/0.9 mmHg (lit.)

density

0.861 g/mL at 25 °C ((lit.))
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]
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]
1S/C10H24N4/c1-11(2)9(12(3)4)10(13(5)6)14(7)8/h1-8H3

InChI key

[CBXRMKZFYQISIV-UHFFFAOYSA-N]
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

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)

127.4 °F - closed cup

Flash Point(C)

53 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ8369
MKCZ7350
MKCX8190
MKCX0947
MKCT7378

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Tetrahedron Letters, 47, 5565-5565 (2006)
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
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
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
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)

四（二甲基氨基）乙烯（TDAE）

在2001年，佛罗里达大学的William Dolbier，Jr.教授报告了一种亲核三氟甲基化的方法，该方法基于在强力双电子还原剂四（二甲基氨基）乙烯（TDAE）存在下使用CF3I生成三氟甲基阴离子。

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