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Reactivity Documentation

Metal Hydrides, Metal Alkyls, Metal Aryls, and Silanes

mixed with

Acyl Halides, Sulfonyl Halides, and Chloroformates

Summary

Details

Reactivity Predictions (for each pair of reactive groups)

Metal Hydrides, Metal Alkyls, Metal Aryls, and Silanes mixed with
Acyl Halides, Sulfonyl Halides, and Chloroformates

Hazard Predictions

LiAlH4 and NaBH4 reduce acid chlorides to flammable alcohols (Kammermeier, B. 2012. Reduction. Ullmann's Encyclopedia of Industrial Chemistry. (Online)).

Tributyl tin hydride (Bu3SnH) and lithium aluminum tri(tert-butoxide) hydride (LiAlH(O-t-C4H9)3) reduce acid chlorides to aldehydes, which may be toxic, volatile, and flammable (Eggeman, T. 2001. Hydrides. In Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. (Online); Kammermeier, B. 2012. Reduction. Ullmann's Encyclopedia of Industrial Chemistry. (Online)).

The reaction of methylmagnesium iodide and thiophosphoryl chloride is highly exothermic and can easily cause an explosion if not adequately controlled (Davies, S.G., Chem. Brit., 1984, 20, 403; Bercaw, J. E., Chem. Eng. News, 1984, 62(18), 4).

Alkylation of acyl halides with dialkylzinc compounds is exothermic and can lead to an explosion if the reaction is too fast or uncontrolled (Methoden der Organischen Chemie; Muller, E. (Ed.); Stuttgart, Thieme, 1973, Vol. 13.2a, p. 781).

Titanium hydride reacts with acid fluoride solutions at elevated temperatures (Sullivan, E. and Wade, R. 1980. Hydrides. Kirk-Othmer Encyclopedia of Chemical Technology, 3rd ed. John Wiley & Sons, Inc.).

Depending on the conditions, lithium aluminum hydride can reduce sulfonyl chlorides to sulfinic acids or thiols (Kammermeier, B. 2000. Reduction. Ullmann's Encyclopedia of Industrial Chemistry. (Online)).

Potential Gas Byproducts