Methylmagnesium chloride

Methylmagnesium chloride
IUPAC name chlorido(methyl)magnesium
Other names (chloromagnesio)methane
Identifiers
CAS number	676-58-4 Y,  75-16-1 (bromide)
ChemSpider	10610396 Y
ChEBI	CHEBI:51492 Y
Jmol-3D images	Image 1
SMILES [Cl-].[Mg+]C
InChI InChI=1S/CH3.ClH.Mg/h1H3;1H;/q;;+1/p-1 Y Key: RQNMYNYHBQQZSP-UHFFFAOYSA-M Y InChI=1/CH3.ClH.Mg/h1H3;1H;/q;;+1/p-1/rCH3Mg.ClH/c1-2;/h1H3;1H/q+1;/p-1 Key: RQNMYNYHBQQZSP-OWCPXFRBAR
Properties
Molecular formula	CH3MgCl
Molar mass	74.79 g/mol
Appearance	colorless solid
Solubility in water	Reacts with water
Solubility	soluble in diethyl ether and THF
Hazards
Main hazards	flammable
Related compounds
Related compounds	Phenylmagnesium bromide
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Methylmagnesium chloride is a commercially available Grignard reagent. Like methyllithium, it is the synthetic equivalent to the methyl carbanion synthon. It is usually sold as a solution in tetrahydrofuran. The model of the molecule shows methylmagnesium chloride with the magnesium atom in the center. Two molecules of tetrahydrofuran (in the upper part of the drawing) coordinate by their oxygen atoms to magnesium.

Like all Grignard reagents, this is a moisture sensitive compound.

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.