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Methylmagnesium chloride
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Methylmagnesium chloride
Methylmagnesium chloride is an organomagnesium compound described with the general formula CH3MgCl. This highly flammable, colorless, and moisture sensitive compound is the simplest Grignard reagent and is commercially available, usually as a solution in tetrahydrofuran.
Relative to the more commonly encountered[citation needed] methylmagnesium bromide and methylmagnesium iodide, methylmagnesium chloride offers the advantages of low equivalent weight and low cost. It is prepared by the reaction of methyl chloride and magnesium in ethyl ether.
As with most Grignard reagents, methylmagnesium chloride is a coordination complex. The Mg center is bonded to two ether ligands to give a tetrahedrally bonded magnesium center.
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.,:
When treated with dioxane, ether solutions of methylmagnesium chloride 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:
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Methylmagnesium chloride
Methylmagnesium chloride is an organomagnesium compound described with the general formula CH3MgCl. This highly flammable, colorless, and moisture sensitive compound is the simplest Grignard reagent and is commercially available, usually as a solution in tetrahydrofuran.
Relative to the more commonly encountered[citation needed] methylmagnesium bromide and methylmagnesium iodide, methylmagnesium chloride offers the advantages of low equivalent weight and low cost. It is prepared by the reaction of methyl chloride and magnesium in ethyl ether.
As with most Grignard reagents, methylmagnesium chloride is a coordination complex. The Mg center is bonded to two ether ligands to give a tetrahedrally bonded magnesium center.
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.,:
When treated with dioxane, ether solutions of methylmagnesium chloride 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: