General Description
A colorless cloudy solution in diethyl ether. Flash point-49°F. Vapors heavier than air.
Reactivity Profile
Organometallics, such as METHYL MAGNESIUM BROMIDE, are reactive with many other groups. Incompatible with acids and bases. Organometallics are good reducing agents and therefore incompatible with oxidizing agents. Often reactive with water to generate toxic or flammable gases.
Air & Water Reactions
Highly flammable. Reacts with water or moisture in the air to form flammable methane gas. The heat from this reaction may be sufficient to ignite the produced methane [AAR 1991]. Unstable peroxides may form with exposure of the ether to air. This is a slow process.
Hazard
Flammable, dangerous fire and explosionrisk.
Health Hazard
Fire will produce irritating, corrosive and/or toxic gases. Inhalation of decomposition products may cause severe injury or death. Contact with substance may cause severe burns to skin and eyes. Runoff from fire control may cause pollution.
Fire Hazard
Flammable/combustible material. May ignite on contact with moist air or moisture. May burn rapidly with flare-burning effect. Some react vigorously or explosively on contact with water. Some may decompose explosively when heated or involved in a fire. May re-ignite after fire is extinguished. Runoff may create fire or explosion hazard. Containers may explode when heated.
Chemical Properties
Clear brown solution when properly stored
Uses
Grignard reagent in greener solvent, 2-methyltetrahydrofuran (2-MeTHF)
Application
Methylmagnesium bromide solution (3M in diethyl ether) be used to synthesize:
3(4R)-{3(2R,3S)-[4′-(1′-triphenylmethyl)imidazole]-2-bromo-1-oxobutyl)-4-phenyl2-oxazolidinone.
Benzyl 2-(2-oxopropyl)piperidine-1-carboxylate.
(R*, R*) 1-[1-(1-phenylethyl)pyrrolidin-2-yl]propan-2-one).
Solubility in organics
Solubility: MeMgBr (Methylmagnesium Bromide) and MeMgI sol Et2O; MeMgCl and MeMgBr sol THF. MgI2 precipitates when MeMgI is prepared in THF, leaving mainly Me2Mg in the solution; some MgCl2 generally precipitates when MeMgCl is prepared in Et2O, particularly if the solution lasts several days. All are insoluble in hydrocarbons.
