Draft:N-Propylmagnesium bromide

n-Propylmagneisum bromide, often referred to as simply propylmagnesium bromide, is an organomagnesium compound with the chemical formula C3H6MgBr. As the Grignard reagent derived from 1-bromopropane, it is used for the n-propylation of electrophiles in organic synthesis.

Properties
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.

Synthesis
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.


 * C3H6\sBr + Mg -> C3H6\sMg\sBr

While the product is often portrayed as simply C3H6MgBr, in reality it will quickly form a tetrahedral coordination complex with the Lewis basic solvent, centred on the magnesium atom:


 * C3H6MgBr + 2 (C2H5)2O -> C3H6Mg((C2H5)2O)2Br
 * C3H6MgBr + 2 (CH2)4O -> C3H6Mg((CH2)4O)2Br

Applications
Propylmagnesium bromide is used in the Grignard reaction to introduce propyl groups to nucleophiles.