Chemistry:Tetraaminoethylene

Short description: Hypothetical organic molecule ((H2N)2C=C(NH2)2)

Tetraaminoethylene

Names
Systematic IUPAC name Ethene-1,1,2,2-tetramine
Other names Ethylenetetraamine
Identifiers
CAS Number	4363-45-5 N
3D model (JSmol)	Interactive image
ChemSpider	11487764 Y
PubChem CID	17899866
InChI InChI=1S/C2H8N4/c3-1(4)2(5)6/h3-6H2 Y Key: XXWSZMQKQLNDLC-UHFFFAOYSA-N Y
SMILES NC(N)=C(N)N
Properties
Chemical formula	C2H8N4
Molar mass	88.114 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

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In organic chemistry, tetraaminoethylene is a hypothetical, organic compound with formula C
2N
4H
8 or (H
2N)
2C=C(NH
2)
2. Like all polyamines that are geminal, this compound has never been synthesised and is believed to be extremely unstable.

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 (R
2N)
2C=C(NR
2)
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 (R
2N)
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 Tetrakis(dimethylamino)ethylene ((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.