Methylmagnesium chloride is an

organometallic Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and ...

compound with the general formula CH₃MgCl. This highly flammable, colorless, and moisture sensitive material is the simplest Grignard reagent and is commercially available, usually as a solution in

tetrahydrofuran Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water- miscible organic liquid with low viscosity. It is ...

Synthesis and reactions

Relative to the more commonly encountered 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. left, Structure of CH₃MgCl(thf)₂, which is representative of the species in donor solvents. As with most Grignard reagents, methylmagnesium chloride is highly solvated by

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again b ...

solvents via

coordination Coordination may refer to: * Coordination (linguistics), a compound grammatical construction * Coordination complex, consisting of a central atom or ion and a surrounding array of bound molecules or ions * Coordination number or ligancy of a centr ...

from two oxygen atoms to give a tetrahedrally bonded magnesium center. Like

methyllithium Methyllithium is the simplest organolithium reagent with the empirical formula CH3Li. This s-block organometallic compound adopts an oligomeric structure both in solution and in the solid state. This highly reactive compound, invariably used in so ...

, it is the synthetic equivalent to the methyl carbanion

synthon In retrosynthetic analysis, a synthon is a hypothetical unit within a target molecule that represents a potential starting reagent in the retroactive synthesis of that target molecule. The term was coined in 1967 by E. J. Corey. He noted in 198 ...

. It reacts with water and other protic reagents to give methane, e.g.,: :CH₃MgCl + ROH → CH₄ + MgCl(OR) When treated with

dioxane 1,4-Dioxane () is a heterocyclic organic compound, classified as an ether. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. The compound is often called simply dioxane because the other dioxane isomers ( 1,2- ...

, ether solutions of methylmagnesium chloride reacts to give the insoluble

coordination polymer A coordination polymer is an inorganic or organometallic polymer structure containing metal cation centers linked by ligands. More formally a coordination polymer is a coordination compound with repeating coordination entities extending in 1, 2, ...

with the formula MgCl₂(dioxane)₂. Remaining in the solution is the dioxane adduct of dimethylmagnesium. This conversion exploits the

Schlenk equilibrium Schlenk can refer to: People * Wilhelm Schlenk (1879-1943), German chemist In chemistry * Schlenk flask * Schlenk line The Schlenk line (also vacuum gas manifold) is a commonly used chemistry apparatus developed by Wilhelm Schlenk. It consist ...

, which is driven to the right by the precipitation of the magnesium halide: :2 CH₃MgCl + 2 dioxane → (CH₃)₂Mg + MgCl₂(dioxane)₂

References

Organomagnesium compounds Methylating agents Methyl complexes

Synthesis and reactions

See also

Further reading

References