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Ethylmagnesium bromide

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Ethylmagnesium bromide
File:Ethylmagnesium bromide.png
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.935 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H5.BrH.Mg/c1-2;;/h1H2,2H3;1H;/q;;+1/p-1Key: TWTWFMUQSOFTRN-UHFFFAOYSA-M
  • InChI=1/C2H5.BrH.Mg/c1-2;;/h1H2,2H3;1H;/q;;+1/p-1/rC2H5BrMg/c1-2-4-3/h2H2,1H3Key: TWTWFMUQSOFTRN-QJSJVVHYAJ
SMILES
  • BrCC
Properties
Chemical formula C2H5BrMg
Molar mass 133.271 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

Ethylmagnesium bromide is a Grignard reagent with formula C2H5MgBr or C2H5Mg·Br, namely a magnesium ion with a covalent bond to an ethyl group and an ionic bond to a bromine anion. It is widely used in the laboratory synthesis of organic compounds.

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:

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:

EtBr + Mg → EtMgBr

References

  1. Taniguchi, H.; Mathai, I. M.; Miller, S. I. "1-Phenyl-1,4-Pentadiyne and 1-Phenyl-1,3-Pentadiyne". Organic Syntheses. 50: 97{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 6, p. 925.
  2. A. J. Quillinan, A. J.; Scheinmann, F. "3-Alkyl-1-alkynes Synthesis: 3-Ethyle-1-hexyne". Organic Syntheses. 58: 1{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 6, p. 595.
  3. Newman, M. S.; Stalick, W. M. "1-Ethoxy-1-butyne". Organic Syntheses. 57: 65{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 6, p. 564.
  4. W. W. Moyer and C. S. Marvel. "Triethyl Carbinol". Organic Syntheses; Collected Volumes, vol. 2, p. 602.
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