Tetrakis(dimethylamino)ethylene

Tetrakis(dimethylamino)ethylene
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
CAS Number	996-70-3;
3D model (JSmol)	Interactive image;
ChemSpider	63634;
ECHA InfoCard	100.012.398
EC Number	213-638-1;
PubChem CID	70455;
UNII	P6737B68MN;
CompTox Dashboard (EPA)	DTXSID0061371 ;
	InChI InChI=1S/C10H24N4/c1-11(2)9(12(3)4)10(13(5)6)14(7)8/h1-8H3 Key: CBXRMKZFYQISIV-UHFFFAOYSA-N;
	SMILES CN(C)C(=C(N(C)C)N(C)C)N(C)C;
Properties
Chemical formula	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
GHS Signal word	Danger
GHS hazard statements	H226, H314
GHS precautionary statements	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

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]

Reactions

TDAE reacts with oxygen in a chemiluminscent reaction to give tetramethylurea[2][3]

Oxidation of TDAE (chemiluminescence).

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⁻]

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References

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

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[1] David M. Lemal (1968). "Tetraaminoethylenes". In Saul Patai (ed.). The Amino Group. pp. 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)