Dimethylmagnesium

Dimethylmagnesium

Names
IUPAC name Dimethylmagnesium
Identifiers
CAS Number	2999-74-8
ChemSpider	10430979
Jmol interactive 3D	Image
PubChem	18141
InChI InChI=1S/2CH3.Mg/h2*1H3; Key: KZLUHGRPVSRSHI-UHFFFAOYSA-N
SMILES C[Mg]C
Properties
Chemical formula	C2H6Mg
Molar mass	54.38 g·mol^−1
Density	0.96 g/cm3
Solubility in water	Reacts
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dimethylmagnesium is an organomagnesium compound. Like other dialkylmagnesium compounds, it is prepared by adding at least one equivalent of dioxane to a solution of methylmagnesium halide:^[1][2]

2 CH₃MgX + dioxane (CH₃)₂Mg + MgX₂(dioxane)

The complex of magnesium dihalide and dioxane precipitates as a solid, driving the Schlenk equilibrium to give the dialkylmagnesium compound, which remains in solution.

The structure of this compound has been determined by X-ray crystallography. The material is a polymer with tetrahedral magnesium centres, each surrounded by bridging methyl groups. The Mg-C distances are 224 pm.^[3]

References

1. Cope, A. C. (1935). "The Preparation of Dialkylmagnesium Compounds from Grignard Reagents". J. Am. Chem. Soc. 57 (11): 2238–2240. doi:10.1021/ja01314a059.
2. Anteunis, M. (1962). "Studies of the Grignard Reaction. II. Kinetics of the Reaction of Dimethylmagnesium with Benzophenone and of Methylmagnesium Bromide-Magnesium Bromide with Pinacolone". J. Org. Chem. 27 (2): 596–598. doi:10.1021/jo01049a060.
3. Weiss, E. (1964). "Die Kristallstruktur des Dimethylmagnesiums". J. Organomet. Chem. 2 (4): 314–321. doi:10.1016/S0022-328X(00)82217-2.