Tetrakis(dimethylamino)ethylene

Tetrakis(dimethylamino)ethylene
Names
	Preferred IUPAC name N1,N1,N′1,N′1,N2,N2,N′2,N′2-Octamethylethene-1,1,2,2-tetramine
	Other names Octamethyl-ethenetetramine; TDAE
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 labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H314
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, 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 ((CH₃)₂N)₂C=C(N(CH₃)₂)₂, It is a colorless liquid. It is classified as an enamine. Primary and secondary enamines tend to isomerize, but tertiary enamines are kinetically stable.^[1] One unusual feature of TDAE is that it is a tetra-enamine. The pi-donating tendency of the amine groups strongly enhances the basicity of the molecule, which does exhibit properties of a typical alkene.^[2]

^ Spitz, Cédric; Terme, Thierry; Vanelle, Patrice (2023). "1,1,2,2-Tetrakis(dimethylamino)ethene". Encyclopedia of Reagents for Organic Synthesis (EROS). doi:10.1002/047084289X. hdl:10261/236866. ISBN 978-0-471-93623-7.
^ David M. Lemal (1968). "Tetraaminoethylenes". In Saul Patai (ed.). The Amino Group. Patai's Chemistry of Functional Groups. pp. 701–748. doi:10.1002/9780470771082. ISBN 9780470771082.

[1] Spitz, Cédric; Terme, Thierry; Vanelle, Patrice (2023). "1,1,2,2-Tetrakis(dimethylamino)ethene". Encyclopedia of Reagents for Organic Synthesis (EROS). doi:10.1002/047084289X. hdl:10261/236866. ISBN 978-0-471-93623-7.

[2] David M. Lemal (1968). "Tetraaminoethylenes". In Saul Patai (ed.). The Amino Group. Patai's Chemistry of Functional Groups. pp. 701–748. doi:10.1002/9780470771082. ISBN 9780470771082.

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