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Reactivity Documentation

Halogenated Organic Compounds

mixed with

Azo, Diazo, Azido, Hydrazine, and Azide Compounds

Summary

Details

Halogenated Organic Compounds is a reactive group.

Reactivity Predictions (for each pair of reactive groups)

Azo, Diazo, Azido, Hydrazine, and Azide Compounds mixed with
Halogenated Organic Compounds

Hazard Predictions

Metal azides may form explosive organic azides if stored for long periods of time in halogenated solvents (Bretherick, L. 1986. Chemical and Engineering News 64(51):2).

Explosions may occur in reactions using NaN3 with methylene chloride/dimethylsulfoxide solvent mixtures. It is not recommended to run reactions with inorganic azides in halogenated organic solvents (Peet, N.P. et al. 1993. Chemical and Engineering News 71916; Hurby, V.J. et al. 1993. Chemical and Engineering News 71(41):2). Bretherick attributes these explosions to the formation of hydrogen azide (HN3) gas (Urben, P.G. 1995. Bretherick's Handbook of Reactive Chemical Hazards, 5th Edition. Oxford: Butterworth-Heinemann. pp. 1700).

Dichloromethane can form explosive diazomethane with quaternary ammonium azides (Hassner, A. et al. 1986. Agnew. Chem. (International Edition.) 25:479-480.).

Chloroform reacts with hydrazine to liberate toxic HCl gas (Zollinger, Heinrich. Azo and Diazo Chemistry. New York: Interscience Publishers, Inc. 1961). Other haloforms may react similarly (Predicted by comparison to similar reactions).

Potential Gas Byproducts