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Ethylmagnesium bromide

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Ethylmagnesium bromide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.935 Edit this at Wikidata
UNII
  • InChI=1S/C2H5.BrH.Mg/c1-2;;/h1H2,2H3;1H;/q;;+1/p-1 checkY
    Key: TWTWFMUQSOFTRN-UHFFFAOYSA-M checkY
  • InChI=1/C2H5.BrH.Mg/c1-2;;/h1H2,2H3;1H;/q;;+1/p-1/rC2H5BrMg/c1-2-4-3/h2H2,1H3
    Key: TWTWFMUQSOFTRN-QJSJVVHYAJ
  • Br[Mg]CC
Properties
C2H5BrMg
Molar mass 133.271 g·mol−1
Hazards
Safety data sheet (SDS) Oxford MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ethylmagnesium bromide is a Grignard reagent with formula C2H5MgBr. It is widely used in the laboratory synthesis of organic compounds.

Reactions

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Apart from acting as the synthetic equivalent of an ethyl anion synthon for nucleophilic addition, ethylmagnesium bromide may be used as a strong base to deprotonate various substrates such as alkynes:[1]

RC≡CH + EtMgBr → RC≡CMgBr + EtH

In this application, ethylmagnesium bromide has been supplanted by the wide availability of organolithium reagents.

Preparation

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Ethylmagnesium bromide is commercially available, usually as a solution in diethyl ether or tetrahydrofuran. It may be prepared in the normal manner of Grignard reagents — by reacting bromoethane with magnesium in diethyl ether:[2]

EtBr + Mg → EtMgBr

References

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  1. ^ Quillinan, A. J.; Scheinmann, F. (1978). "3-Alkyl-1-alkynes Synthesis: 3-Ethyle-1-hexyne". Organic Syntheses. 58: 1; Collected Volumes, vol. 6, p. 595.
  2. ^ Moyer, W. W.; Marvel, C. S. (1931). "Triethyl Carbinol". Organic Syntheses. 11: 98; Collected Volumes, vol. 2, p. 602.