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Hazard Predictions

• Generates heat: Exothermic reaction at ambient temperatures (releases heat)
• Toxic: Reaction products may be toxic

The combination of organometallics and nitriles may be incompatible. 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.

Lithium cuprates (i.e. Li[CuR2]) can add a copper-carbon bond across the carbon-nitrogen triple bond of a nitrile, forming a copper-bound amine (Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 4th ed.; Wiley-Interscience: Hoboken (NJ), 2005, p. 426-7).

When triiron dodecacarbonyl and 2,4-hexadienenitrile were combined, the product consisted of iron tricarbonyl coordinated to the double bonds, and the nitrile functionality remained unchanged (King, R.B., Manuel, T. A., Stone, F. G. A.; J. lnorg. Nucl. Chem.; 1961; Vol. 16; pp. 233 to 239).