Methylmagnesium chloride
Template:Chembox Methylmagnesium chloride is an organometallic compound with the general formula Template:Chem2. This highly flammable, colorless, and moisture sensitive compound is the simplest Grignard reagent and is commercially available, usually as a solution in tetrahydrofuran.
Synthesis and reactions
Relative to the more commonly encountered methylmagnesium bromide[1] 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.[2]
As with most Grignard reagents, methylmagnesium chloride is highly solvated by ether solvents via coordination from two oxygen atoms 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 Template:Chem2. 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:[3]
See also
Further reading
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