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Hazard Predictions

• Generates heat: Exothermic reaction at ambient temperatures (releases heat)

The combination of aniline with organometallic compounds may result in exothermic ligand exchange reactions. 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.

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

Aniline coordinates to palladium complexes. This is the first step of the Buchwald-Hartwig catalytic amination reaction. However, for the other steps of the reaction to occur, other reagents are required such as a strong base and an aryl halide (Behr, A. 2010. Catalysis, Homogeneous. Ullmann's Encyclopedia of Industrial Chemistry. (Online)).