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]
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| ECHA InfoCard | 100.011.967 |
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CompTox Dashboard (EPA)
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| 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).
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Properties
editLike 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
editSynthesis 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
editPropylmagnesium bromide is used in the Grignard reaction to introduce propyl groups to nucleophiles.[1]
References
edit- ^ 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.
- ^ Macintyre, Jane E. (10 November 1994). Dictionary of Organometallic Compounds. CRC Press. p. 2275. ISBN 978-0-412-43060-2.
- ^ 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.