Methylmagnesium chloride
Names | |
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IUPAC name
chlorido(methyl)magnesium
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Other names
(chloromagnesio)methane
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.010.573 |
EC Number |
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PubChem CID
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UNII |
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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 | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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Flammable, Reacts with water |
GHS labelling: | |
Danger | |
H225, H250, H260, H314 | |
P210, P222, P223, P231+P232, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P334, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P335+P334, P363, P370+P378, P402+P404, P403+P235, P405, P422, P501 | |
NFPA 704 (fire diamond) | |
Flash point | −17 °C (1 °F; 256 K) |
Related compounds | |
Related compounds
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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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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.
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]
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.,:
- CH3MgCl + ROH → CH4 + MgCl(OR)
When treated with dioxane, methylmagnesium chloride converts to dimethylmagnesium via the Schlenk equilibrium:
- 2 CH3MgCl + dioxane → (CH3)2Mg + MgCl2(dioxane)
See also
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
- ^ "(E)-4-Hexen-1-ol". Org. Synth. 55: 62. 1976. doi:10.15227/orgsyn.055.0062.
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(help) - ^ E. R. Coburn (1947). "3-Penten-2-ol". Org. Synth. 27: 65. doi:10.15227/orgsyn.027.0065.