Methylmagnesium bromide is an organomagnesium compound described with the general formula CH3MgBr. It is a colorless and moisture-sensitive compound. It is one of the simplest Grignard reagents. It is commercially available as a solution in tetrahydrofuran (thf).
Synthesis and reactions It is prepared by the reaction of methyl bromide and magnesium in ethyl ether. and methylmagnesium iodide, methylmagnesium chloride offers the advantages of low equivalent weight and low cost. Like methyllithium, it is the synthetic equivalent to the methyl carbanion synthon. It reacts with water, alcohols and other protic reagents to give methane, e.g.,:
CH3MgBr + ROH → CH4 + "ROMgBr" When treated with dioxane, ether solutions of methylmagnesium bromide reacts to give the insoluble coordination polymer with the formula MgCl2(dioxane)2. Remaining in the solution is the dioxane adduct of dimethylmagnesium. This conversion exploits the Schlenk equilibrium, which is driven to the right by the precipitation of the magnesium halide:
2 CH3MgBr + 2 dioxane → (CH3)2Mg + MgBr2(dioxane)2
Structure As with most Grignard reagents, methylmagnesium bromide is usually deployed as a complex containing ether or thf as ligands. In these etherial solutions multiple species may coexist. The trigonal bipyramidal complex CH3MgBr(thf)3 has been crystallized and identified by X-ray crystallography.
See also Methylation Methylmagnesium chloride
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