Jump to content

n-Propylmagnesium bromide

From Wikipedia, the free encyclopedia
(Redirected from Propylmagnesium bromide)
n-Propylmagnesium bromide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.967 Edit this at Wikidata
EC Number
  • 213-162-4
  • InChI=1S/C3H7.BrH.Mg/c1-3-2;;/h1,3H2,2H3;1H;/q-1;;+2/p-1
    Key: UGVPKMAWLOMPRS-UHFFFAOYSA-M
  • CC[CH2-].[Mg+2].[Br-]
Properties
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).

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.[1]

Properties

[edit]

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

[edit]

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]

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

[edit]

Propylmagnesium bromide is used in the Grignard reaction to introduce propyl groups to nucleophiles.[1]

References

[edit]
  1. ^ a b c Maruyama, Kazuhiro; Matano, Yoshihiro; Katagiri, Toshimasa (August 1991). "Product-determining factors in the grignard reactions of benzophenones. The role of the structure of alkyl groups in grignard reagents". Journal of Physical Organic Chemistry. 4 (8): 501–515. doi:10.1002/poc.610040806.
  2. ^ Macintyre, Jane E. (10 November 1994). Dictionary of Organometallic Compounds. CRC Press. p. 2275. ISBN 978-0-412-43060-2.
  3. ^ Canonne, P.; Foscolos, G.; Caron, H.; Lemay, G. (January 1982). "Etude de l'influence du diluant hydrocarbone dans la reaction des organomagnesiens primaires sur les cetones encombrees". Tetrahedron. 38 (24): 3563–3568. doi:10.1016/0040-4020(82)80061-6.