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Ethylmagnesium bromide

From Wikipedia, the free encyclopedia

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).
checkY verify (what is checkY☒N ?)

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

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  • Which of the following compounds reacts with ethylmagnesium bromide and also decolourizes bromine
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  • M.S.Chouhan Solution - Grignard Reagents : Q18,Q19,Q20 & Q21.

Transcription

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; Collected Volumes, vol. 6, p. 925.
  2. ^ 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.
  3. ^ Newman, M. S.; Stalick, W. M. (1977). "1-Ethoxy-1-butyne". Organic Syntheses. 57: 65; Collected Volumes, vol. 6, p. 564.
  4. ^ Moyer, W. W.; Marvel, C. S. (1931). "Triethyl Carbinol". Organic Syntheses. 11: 98; Collected Volumes, vol. 2, p. 602.
This page was last edited on 10 March 2024, at 16:31
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