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Ethylmagnesium bromide

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This is the current revision of this page, as edited by DMacks (talk | contribs) at 23:10, 30 July 2024 (→Reactions: BuLi is used as the base not EtMgBr, it's deprotonating at the propargylic position not the alkyne itself (though this would be a novel use worth mentioning if EtMgBr were involved). the only ethyl is EtBr as electrophile.). The present address (URL) is a permanent link to this version.

Revision as of 23:10, 30 July 2024 by DMacks (talk | contribs) (→Reactions: BuLi is used as the base not EtMgBr, it's deprotonating at the propargylic position not the alkyne itself (though this would be a novel use worth mentioning if EtMgBr were involved). the only ethyl is EtBr as electrophile.)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
Ethylmagnesium bromide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.935 Edit this at Wikidata
PubChem CID
UNII
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
Hazards
Safety data sheet (SDS) Oxford MSDS
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. 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. 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.
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