674613

Sigma-Aldrich

Tetrakis(dimethylamino)ethylene

Synonym(s):
Octamethylethylenetetramine, TDAE
Linear Formula:
[(CH3)2N]2C=C[N(CH3)2]2
CAS Number:
Molecular Weight:
200.32
Beilstein/REAXYS Number:
1705900
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.)

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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Related Categories

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.

Packaging

1, 10, 50 g in glass bottle

Pictograms

FlameCorrosion

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2734PSN1 3(8) / PGII

WGK Germany

WGK 3

Flash Point(F)

127.4 °F - closed cup

Flash Point(C)

53 °C - closed cup

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...
Articles
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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