Tetrakis(dimethylamino)ethylene

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]

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

Reactions

TDAE reacts with oxygen in a chemiluminescent reaction to give tetramethylurea.^[3][4] The initial intermediate is (2+2) adduct, a 1,2-dioxetane. This species decomposes to electronically excited tetramethylurea. This returns to the ground state is accompanied by emission of green light with a maximum at 515 nm.^[5]

Oxidation of TDAE (chemiluminescence).

TDAE is an electron donor with E = 1.06 V vs Fc^+/0.^[6]

TDAE has been examined as a reductant in coupling reactions.^[7]

As one of many of examples of its redox behavior forms a charge-transfer salt with buckminsterfullerene:^[8]

C₂(N(CH₃)₂)₄ + C₆₀ → [C₂(N(CH₃)₂)₄⁺][C₆₀⁻] Oxidation affords a dication.

Structure

Crystallographic analysis show that TDAE is a highly distorted alkene, the dihedral angle for the two N2C termini is 28°. The C=C distance is alkene-like, 135 pm. The nearly isostructural tetraisopropylethylene also has a C=C distance of 135 pm, but its C6 core is planar. In contrast, [TDAE]²⁺ is an alkane with multi-C-N bonds.^[9]

Structure of TDAE and its dication (distances in picometers).^[9]

Synthesis

It is available by pyrolysis of tris(dimethylamino)methane by pyrolysis^[10] or from chlorotrifluoroethene and dimethylamine.^[11]