Tetraaminoethylene

Tetraaminoethylene

Names
Systematic IUPAC name Ethene-1,1,2,2-tetramine[1]
Other names Ethylenetetraamine
Identifiers
CAS Number	4363-45-5
ChemSpider	11487764
Jmol interactive 3D	Image
PubChem	17899866
InChI InChI=1S/C2H8N4/c3-1(4)2(5)6/h3-6H2 Key: XXWSZMQKQLNDLC-UHFFFAOYSA-N
SMILES NC(N)=C(N)N
Properties
Chemical formula	C2H8N4
Molar mass	88.11 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Tetraaminoethylene is a hypothetical organic compound with formula C₂N₄H₈ or (H₂N-)₂C=C(-NH₂)₂. Like all geminal polyamines, this compound has never been synthesised and is believed to be extremely unstable.^[2]

However, there are many stable compounds that can be viewed as derivatives of tetraaminoethylene, with various organic functional groups substituted for some or all hydrogen atoms. These compounds, which have the general formula (R₂N)₂C=C(NR₂)₂, are collectively called tetraaminoethylenes.

General chemical structure of tetraaminoethylene derivatives

Tetraaminoethylenes are important in organic chemistry as dimers of diaminocarbenes, a type of stable carbene with the general formula (R₂N)₂C:.

Reactions

• Tetraaminoethylenes react with acids to give formamidinium salts.
• Tetraaminoethylenes react with oxygen to give urea derivatives (R₂N)₂C=O. A notorious example is the spontaneous reaction of octamethyltetraminoethylene ((H₃C-)₂N-)₂C=C(-N(-CH₃)₂)₂ in air with emission of a green-blue light, which was used by downed US Navy pilots to signal for help in World War II.

References

1. "CID 17899866 - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
2. Stephen A. Lawrence (2004), Amines: synthesis, properties and applications. Cambridge University Press. ISBN 0-521-78284-8, 371 pages.