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
CAS Number	1730-25-2 Y
3D model (JSmol)	Interactive image
ChemSpider	10796765 Y
ECHA InfoCard	100.015.497
PubChem CID	74413
CompTox Dashboard (EPA)	DTXSID30938266
InChI InChI=1S/C3H5.BrH.Mg/c1-3-2;;/h3H,1-2H2;1H;/q;;+1/p-1 Y Key: FEMBXICCJNZMMC-UHFFFAOYSA-M Y 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
SMILES [Br-].[Mg+]CC=C
Properties
Chemical formula	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). Y verify (what is YN ?) 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. 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.