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Tetrakis(dimethylamino)ethylene (TDAE) is an organic compound with the formula C2(N(CH3)2)4. It is a colorless liquid. It is classified as an enamine.

Tetrakis(dimethylamino)ethylene
C2(NMe2)4.png
Names
IUPAC name
1-N,1-N,1-N',1-N',2-N,2-N,2-N',2-N'-octamethylethene-1,1,2,2-tetramine
Other names
Octamethyl-ethenetetramine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.398
EC Number 213-638-1
UNII
Properties
C10H24N4
Molar mass 200.330 g·mol−1
Appearance colorless liquid
Density 0.861 g/cm3 (25 °C)
Melting point −4 °C (25 °F; 269 K)
Boiling point 59 °C (0.9 mm Hg)
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word Danger
H226, H314
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P363, P370+378, P403+235, P405, P501
Flash point 53 °C (127 °F; 326 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

ReactionsEdit

TDAE reacts with oxygen in a chemiluminscent reaction to give tetramethylurea[1][2]

TDAE is an electron donor. It forms a charge transfer salt with buckminsterfullerene:[3]

C2(N(CH3)2)4 + C60 → [C2(N(CH3)2)4+][C60]

ReferencesEdit

  1. ^ H.E. Winberg; J. R. Downing; D. D. Coffman (1965). "The Chemiluminescence of Tetrakis(dimethylamino)ethylene". J. Am. Chem. Soc. 87: 2054–2055. doi:10.1021/ja01087a039.
  2. ^ "Chemilumineszenz von TDAE" (in German). illumina-chemie.de. 2014-08-08. Retrieved 2016-08-22.
  3. ^ Allemand, P.-M.; Khemani, K. C.; Koch, A.; Wudl, F.; Holczer, K.; Donovan, S.; GrÜner, G.; Thompson, J. D. (1991). "Organic Molecular Soft Ferromagnetism in a Fullerene". Science. 253: 301. doi:10.1126/science.253.5017.301.CS1 maint: Uses authors parameter (link)