Ethylmagnesium bromide

Ethylmagnesium bromide is a Grignard reagent with formula C2H5MgBr. It is widely used in the laboratory synthesis of organic compounds.

Ethylmagnesium bromide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.935
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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Infobox references

Reactions

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][2][3]

RC≡CH + EtMgBr → RC≡CMgBr + EtH

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

Preparation

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:[4]

EtBr + Mg → EtMgBr

References
  1. Taniguchi, H.; Mathai, I. M.; Miller, S. I. (1970). "1-Phenyl-1,4-Pentadiyne and 1-Phenyl-1,3-Pentadiyne". Organic Syntheses. 50: 97.; Collective Volume, vol. 6, p. 925
  2. Quillinan, A. J.; Scheinmann, F. (1978). "3-Alkyl-1-alkynes Synthesis: 3-Ethyle-1-hexyne". Organic Syntheses. 58: 1.; Collective Volume, vol. 6, p. 595
  3. Newman, M. S.; Stalick, W. M. (1977). "1-Ethoxy-1-butyne". Organic Syntheses. 57: 65.; Collective Volume, vol. 6, p. 564
  4. Moyer, W. W.; Marvel, C. S. (1931). "Triethyl Carbinol". Organic Syntheses. 11: 98.; Collective Volume, vol. 2, p. 602
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