Tetramethylethylenediamine

Tetramethylethylenediamine (often abbreviated as TMEDA or TEMED) is a chemical compound with the formula (CH3)2NCH2CH2N(CH3)2. This species is derived from ethylene by replacement of the four hydrogen atoms with methyl groups and two nitrogen atoms. It is a colorless liquid, although old samples often appear yellow. TMEDA is a widely used building block in organic synthesis and an excellent ligand for transition metal ions.

Structure and bonding

TMEDA is a bidentate ligand towards many metal ions. Its complexes are usually diamagnetic and adopt tetrahedral geometry. The nitrogen centers are not equivalent in these complexes, reflecting the greater basicity of the nitrogen center that is more distant from the substituents on the nitrogen.

Uses

TMEDA is commonly used as a ligand for the synthesis of transition metal complexes. It is also used as a reagent in organic synthesis, for example as an accelerator in the curing of epoxy resins.

Safety

TMEDA is flammable, and its mixtures with air are potentially explosive. It can cause burns to skin and eyes, and if ingested or inhaled it can be harmful.

See also

• Ethylenediamine
• Diethylenetriamine
• Triethylenetetramine

References

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  Tetramethylethylenediamine
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  LiHMDS-tmeda complex
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  Doyle catalyst