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 so ...

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 ma ...

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 Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an organic compound with the chemical formula . One of the haloalkanes, it is a colorless, odorless, flammable gas. Methyl chloride is a crucial reagent in industria ...

and magnesium in

ethyl ether Diethyl ether, or simply ether, is an organic compound in the ether class with the formula , sometimes abbreviated as (see Pseudoelement symbols). It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable liq ...

. 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 be c ...

solvents via coordination 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 In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...

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 1 ...

. 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 with the formula MgCl₂(dioxane)₂. Remaining in the solution is the dioxane adduct of

dimethylmagnesium Dimethylmagnesium is an organomagnesium compound. It is a white pyrophoric solid. Dimethylmagnesium is used in the synthesis of organometallic compounds. Preparation Like other dialkylmagnesium compounds, dimethylmagnesium is prepared by adding d ...

. This conversion exploits the

Schlenk equilibrium Schlenk can refer to: People * Wilhelm Schlenk (1879-1943), German chemist In chemistry * Schlenk flask * Schlenk line. or Schlenk apparatus * Schlenk equilibrium Other * Mepco Schlenk Engineering College MEPCO may refer to: * Mepco Schlenk En ...

, 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