Methylmagnesium chloride is an organometallic 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.
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Names | |
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IUPAC name chlorido(methyl)magnesium | |
Other names (chloromagnesio)methane | |
Identifiers | |
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3D model ( JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.010.573 ![]() |
PubChemCID | |
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CompTox Dashboard(EPA) | |
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Properties | |
CH3MgCl | |
Molar mass | 74.79 g/mol |
Appearance | colorless solid |
Reacts with water | |
Solubility | soluble in diethyl ether and THF |
Hazards | |
Main hazards | Flammable, Reacts with water |
NFPA 704 (fire diamond) | |
Flash point | -17°C |
Related compounds | |
Related compounds | Phenylmagnesium bromide, Dibutylmagnesium |
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 | |
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]
![](http://wikiimg.tojsiabtv.com/wikipedia/commons/thumb/3/3b/Methylmagnesium-chloride-THF-3D-balls.png/220px-Methylmagnesium-chloride-THF-3D-balls.png)
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 and other protic reagents to give methane, e.g.,:
- CH 3MgCl + ROH → CH 4 + MgCl(OR)
When treated with dioxane, methylmagnesium chloride converts to dimethylmagnesium via the Schlenk equilibrium:
- 2 CH 3MgCl + dioxane → (CH 3) 2Mg + MgCl 2(dioxane)
See also
- Methylation
Further reading
- Sakai, Shogo; Jordan, K. D. (1982). "Ab initio study of the structure and vibrational frequencies of the Grignard reagent methylmagnesium chloride". Journal of the American Chemical Society. 104 (14): 4019. doi:10.1021/ja00378a047.
References
- ^ Raymond Paul, Olivier Riobé, Michel Maumy (1976). "(E)-4-Hexen-1-ol". Org. Synth. 55: 62. doi:10.15227/orgsyn.055.0062.CS1 maint: uses authors parameter (link)
- ^ E. R. Coburn (1947). "3-Penten-2-ol". Org. Synth. 27: 65. doi:10.15227/orgsyn.027.0065.