Allylmagnesium bromide

Allylmagnesium bromide is a Grignard reagent used for introducing the allyl group. It is commonly available as a solution in diethyl ether. It may be synthesized by treatment of magnesium with allyl bromide while maintaining the reaction temperature below 0 °C to suppress formation of hexadiene.[1] Allyl chloride can also be used in place of the bromide to give allylmagnesium chloride.[2] These reagents are used to prepare metal allyl complexes.

Allylmagnesium bromide
Names
IUPAC name
Allylmagnesium bromide
Systematic IUPAC name
Prop-2-enylmagnesium bromide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.497
  • InChI=1S/C3H5.BrH.Mg/c1-3-2;;/h3H,1-2H2;1H;/q;;+1/p-1 checkY
    Key: FEMBXICCJNZMMC-UHFFFAOYSA-M checkY
  • InChI=1/C3H5.BrH.Mg/c1-3-2;;/h3H,1-2H2;1H;/q;;+1/p-1/rC3H5Mg.BrH/c1-2-3-4;/h2H,1,3H2;1H/q+1;/p-1
    Key: FEMBXICCJNZMMC-NCRCPWRRAY
  • [Br-].[Mg+]CC=C
Properties
C3H5BrMg
Molar mass 145.282 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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Infobox references

References
  1. Benson, R. E.; McKusick, B. C. (1958). "1,4-Pentadiene". Organic Syntheses. 38: 78.
  2. O'Brien, S.; Fishwick, M.; McDermott, B.; Wallbridge, M. G. H.; Wright, G. A. (1972). "Isoleptic Allyl Derivatives of Various Metals". Inorganic Syntheses. Inorganic Syntheses. Vol. 13. pp. 73–79. doi:10.1002/9780470132449.ch14. ISBN 9780470132449.

Further reading
  • Chabot, P. (1996). "7. Infrared and Raman Spectroscopy". In Rakita, P. E.; Silverman, G. (eds.). Handbook of Grignard Reagents. New York, N.Y.: Marcel Dekker. pp. 93–102. ISBN 0-8247-9545-8.
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