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Hazard Predictions

• Corrosive: Reaction products may be corrosive
• Flammable: Reaction products may be flammable
• Generates heat: Exothermic reaction at ambient temperatures (releases heat)

A vigorous reaction occurs on heating N,N-dimethylformamide (DMF) with sodium metal (Bretherick L., Bretherick's Handbook of Reactive Chemical Hazards, Fifth Ed., Urben, P.G., Ed.; Butterworth-Heinemann, Boston, MA, 1996).

Sodium performs stepwise one-electron reductions of some amides, creating reactive radical intermediates (A. J. Birch, J. Cymerman-Craig, M. Slayton. Aust. J. Chem. 1955, 8, 512). In the presence of proton sources (esp. alcohol solvents), the reaction produces amines and aldehydes, which may be further reduced to alcohols and alkoxides (L. Bouveault and G. Blanc, Comptes rendus. 1903, 136, 1676).

Potential Gas Byproducts

• Alcohols
• Aldehydes
• Ammonia (NH3)