Dimethylmagnesium

Dimethylmagnesium
Names
	IUPAC name Dimethylmagnesium
Identifiers
CAS Number	2999-74-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	10430979 ;
PubChem CID	18141;
CompTox Dashboard (EPA)	DTXSID0062765 ;
	InChI InChI=1S/2CH3.Mg/h2*1H3; Key: KZLUHGRPVSRSHI-UHFFFAOYSA-N ;
	SMILES C[Mg]C;
Properties
Chemical formula	C2H6Mg
Molar mass	54.375 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. It is a white pyrophoric solid.

Preparation

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)

Addition of 0.5 molar equivalents of 1,4-dioxane causes precipitation of MgX₂ as an insoluble dioxane-adduct, driving the Schlenk equilibrium to (CH₃)₂Mg.

It can also be prepared by treating calcium, magnesium and methyl iodide in diethyl ether or by combining dimethyl mercury and magnesium.[3][4]

Properties

The structure of this compound has been determined by X-ray crystallography. The material is a polymer with the same connectivity as silicon disulfide, featuring tetrahedral magnesium centres, each surrounded by bridging methyl groups. The Mg-C distances are 224 pm.[5] Dimethylberylium adopts the same structure.[6]

References

Cope, A. C. (1935). "The Preparation of Dialkylmagnesium Compounds from Grignard Reagents". J. Am. Chem. Soc. 57 (11): 2238–2240. doi:10.1021/ja01314a059.
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.
[, p. 215, at Google Books Houben-Weyl Methods of Organic Chemistry Vol. XIII/2a, 4th Edition Organometallic Compounds of Group II of the Periodic Table (except mercury)] Check |url= value (help) (in German), Georg Thieme Verlag, 2014, p. 215, ISBN 978-3-13-180654-3
Jane E. Macintyre (1994), [, p. 2273, at Google Books Dictionary of Organometallic Compounds] Check |url= value (help) (in German), CRC Press, p. 2273, ISBN 978-0-412-43060-2
Weiss, E. (1964). "Die Kristallstruktur des Dimethylmagnesiums". J. Organomet. Chem. 2 (4): 314–321. doi:10.1016/S0022-328X(00)82217-2.
Snow, A.I.; Rundle, R.E. (1951). "Structure of Dimethylberyllium". Acta Crystallographica. 4 (4): 348–52. doi:10.1107/S0365110X51001100. hdl:2027/mdp.39015095081207.

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[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] [, p. 215, at Google Books Houben-Weyl Methods of Organic Chemistry Vol. XIII/2a, 4th Edition Organometallic Compounds of Group II of the Periodic Table (except mercury)] Check |url= value (help) (in German), Georg Thieme Verlag, 2014, p. 215, ISBN 978-3-13-180654-3

[Jane_E._Macintyre-4] Jane E. Macintyre (1994), [, p. 2273, at Google Books Dictionary of Organometallic Compounds] Check |url= value (help) (in German), CRC Press, p. 2273, ISBN 978-0-412-43060-2

[5] Weiss, E. (1964). "Die Kristallstruktur des Dimethylmagnesiums". J. Organomet. Chem. 2 (4): 314–321. doi:10.1016/S0022-328X(00)82217-2.

[6] Snow, A.I.; Rundle, R.E. (1951). "Structure of Dimethylberyllium". Acta Crystallographica. 4 (4): 348–52. doi:10.1107/S0365110X51001100. hdl:2027/mdp.39015095081207.