n-Propylmagnesium bromide, often referred to as simply propylmagnesium bromide, is an organomagnesium compound with the chemical formula . As the Grignard reagent derived from 1-bromopropane, it is used for the n-propylation of electrophiles in organic synthesis.[1]
Like all Grignard reagents, propylmagnesium bromide is a strong electrophile, sensitive to both water and air.
The propylmagnesium halides are the simplest Grignard reagents to exhibit isomerism. Isopropylmagnesium chloride is the primary synthetic equivalent of the isopropyl group.[1]
n-Propylmagnesium bromide is soluble in ether, tetrahydrofuran, and toluene.[2]
Synthesis is analogous to other saturated alkyl Grignard reagents. A solution of 1-bromopropane in ether - typically diethyl ether or tetrahydrofuran - is treated with magnesium, which inserts itself into the organohalogen bond. As both the magnesium metal and the product are sensitive to water, the reaction must take place in anhydrous conditions.[3]
While the product is often portrayed as simply, in reality it will quickly form a tetrahedral coordination complex with the Lewis basic solvent, centred on the magnesium atom:
Propylmagnesium bromide is used in the Grignard reaction to introduce propyl groups to nucleophiles.[1]