Phenylmagnesium Bromide

"Phenylmagnesium bromide, with the simplified formula C₆H₅MgBr, is a magnesium-containing organometallic compound. It is so commonly used that it is commercially available as a solution in diethyl ether or tetrahydrofuran (THF). Phenylmagnesium bromide is a Grignard reagent. It is often used as a synthetic equivalent for the phenyl "Ph^–" synthon."

"Although phenylmagnesium bromide is routinely represented as C₆H₅MgBr, the molecule is more complex. The compound invariably forms an adduct with two OR₂ ligands from the ether or THF solvent. Thus, the Mg is tetrahedral and obeys the octet rule. The Mg–O distances are 201 and 206 pm whereas the Mg–C and Mg–Br distances are 220 pm and 244 pm, respectively."