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Allylmagnesium bromide

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Allylmagnesium bromide
Names
IUPAC name Allylmagnesium bromide
Systematic IUPAC name Prop-2-enylmagnesium bromide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.497 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H5.BrH.Mg/c1-3-2;;/h3H,1-2H2;1H;/q;;+1/p-1Key: FEMBXICCJNZMMC-UHFFFAOYSA-M
  • 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-1Key: FEMBXICCJNZMMC-NCRCPWRRAY
SMILES
  • .CC=C
Properties
Chemical formula C3H5BrMg
Molar mass 145.282 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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. Allyl chloride can also be used in place of the bromide to give allylmagnesium chloride. These reagents are used to prepare metal allyl complexes.

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. 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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