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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.[1]

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 GHS02: FlammableGHS05: Corrosive
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[2][3]

TDAE is an electron donor. It forms a charge transfer salt with buckminsterfullerene:[4]

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

ReferencesEdit

  1. ^ David M. Lemal (1968). "Tetraaminoethylenes". In Saul Patai (ed.). The Amino Group. p. 701-748. doi:10.1002/9780470771082. ISBN 9780470771082.
  2. ^ 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.
  3. ^ "Chemilumineszenz von TDAE" (in German). illumina-chemie.de. 2014-08-08. Retrieved 2016-08-22.
  4. ^ 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)