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Hazard Predictions

• Generates gas: Reaction liberates gaseous products and may cause pressurization
• Generates heat: Exothermic reaction at ambient temperatures (releases heat)

For less-active organometallic compounds (i.e. those that are not metal hydrides or highly active metal alkyls), weak bases mostly serve as coordinating ligands which bind to the metal and do not otherwise react. Caution should be used before proceeding. Further research of comparable examples in the literature or very small scale, carefully controlled experiments may be needed to fully assess compatibility.

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)).

Potential Gas Byproducts

• Hydrocarbons