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Hazard Predictions

• No known hazardous reaction

For less-active organometallic compounds (i.e. those that are not metal hydrides or highly active metal alkyls), amines mostly serve as coordinating ligands which bind to the metal and do not otherwise react.

Mixture of n-butyllithium and coordinating bases such as amines and phosphines result in coordination complexes that break up the aggregate structure of butyllithium and increase its reactivity (Quirk, R. P. and Monroy, V. M. 2004. Initiators, Anionic. Kirk-Othmer Encyclopedia of Chemical Technology. (Online)).

By adding Lewis bases such as TMEDA to the hexamer of n-BuLi, the oligomers are separated into monomers and lithium is coordinated by nitrogen atoms. This leads to higher polarization of the Li-C bond, which in turn increases the reactivity of the strongly carbanionic butyl group and accelerates the reaction rate (Salzer, A. 2010. Organometallic Compounds. Ullmann's Encyclopedia of Industrial Chemistry. (Online)).