Draft:N-Propylmagnesium bromide

N-Propylmagnesium bromide

Identifiers
CAS Number	927-77-5
3D model (JSmol)	Interactive image
ChemSpider	10265325
EC Number	213-162-4
PubChem CID	101916
InChI InChI=1S/C3H7.BrH.Mg/c1-3-2;;/h1,3H2,2H3;1H;/q-1;;+2/p-1 Key: UGVPKMAWLOMPRS-UHFFFAOYSA-M
SMILES CC[CH2-].[Mg+2].[Br-]
Properties
Chemical formula	C3H7BrMg
Molar mass	147.298 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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−Br + Mg → C₃H₆−Mg−Br

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.