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Reactivity Documentation

Amides and Imides

mixed with

Halogenating Agents

Summary

Details

Amides and Imides is a reactive group.
Halogenating Agents is a reactive group.

Reactivity Predictions (for each pair of reactive groups)

Amides and Imides mixed with
Halogenating Agents

Hazard Predictions

DMF reacts exothermically with Br2, possibly forming toxic and flammable carbon monoxide gas and toxic HBr gas (Tayim, H.A. et al. 1973. Chemistry and Industry 347.).

DMF reacts exothermically with Cl2, producing toxic and flammable carbon monoxide gas and inert CO2 gas (Woltornist, A. 1983. Chemical and Engineering News 61(6):4.).

Elevated temperature or iron impurities allow an exothermic reaction between DMF and thionyl chloride. Reaction evolves toxic SO2 gas (Spitulink, M.J. 1977. Chemical and Engineering News 55(31):31; Joshi, M.S. 1986. Chemical and Engineering News 64(25):4.).

Urea can explode if heated with PCl5, probably due to formation of NCl3. Generally related also to other chlorinating agents and nitrogen compounds (Anon. 1960. Agnew. Chem. (Nachr.) 8:33.).

DMF forms toxic dimethylcarbamoyl chloride, a suspected carcinogen, with thionyl chloride or phosphorus oxychloride. Thionyl chloride reaction can result in overpressure if Fe or Zn is present (Marsella, J. A. 2000. Dimethylformamide. Kirk-Othmer Encyclopedia of Chemical Technology. (Online)).

Formamide may react with phosphorus pentabromide to form toxic HCN and CH3Br gases (Smith, P. A. S., Open-Chain Nitrogen Compounds, Vol. I. New York: W. A. Benjamin, Inc., 1965, pp. 148).

Potential Gas Byproducts