10234. Tetrakis(dimethylamino)ethylene

Nomenclature

CAS number: 996-70-3
N1,N1,N′1,N′1,N2,N2,N′2,N′2-Octamethyl-1,1,2,2-ethenetetramine; TDAE; tetrakis(dimethylamino)ethene.
C10H24N4; mol wt 200.32.
C 59.96%, H 12.08%, N 27.97%.

Description and references

Organic reductant; alternative to zinc as an electron donor. Prepn: R. L. Pruett et al., J. Am. Chem. Soc. 72, 3646 (1950) DOI. Structural study: H. Bock et al., Angew. Chem. Int. Ed. 28, 1684 (1989) DOI. Thermodynamic properties: W. V. Steele et al., J. Chem. Eng. Data 42, 1037 (1997) DOI. Cyclic voltammetry and applications in organofluorine synthesis: C. Burkholder et al., J. Org. Chem. 63, 5385 (1998) DOI. Synthetic applications: G. Pawelke, J. Fluorine Chem. 42, 429 (1989) DOI; M. Kuroboshi et al., J. Org. Chem. 68, 3938 (2003) DOI PubMed; M. Médebielle et al., Tetrahedron Lett. 44, 7871 (2003) DOI; Y. Nishiyama, A. Kobayashi, ibid. 47, 5565 (2006) DOI. Review of reactivity: N. Wiberg, Angew. Chem. Int. Ed. 7, 766-779 (1968) DOI.

Chemical structure

Properties

Pale green liquid, bp0.9 59°. nD25 1.4785. d425 0.8612. Flash pt, closed cup: 127.4°F (53°C). Corrosive, flammable. Ionization potential: 6.13 eV.

Use

In reduction of organofluorine compounds; as a radical generator in organic synthesis; in detection of scintillation light from gas scintillation proportional counters.