Ethylmagnesium bromide

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Ethylmagnesium bromide
Ethylmagnesium bromide.png
Identifiers
925-90-6 YesY
ChemSpider 10254342 YesY
Jmol-3D images Image
PubChem 101914
Properties
C2H5BrMg
Molar mass 133.27 g·mol−1
Hazards
Safety data sheet 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

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[edit]

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[edit]

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[edit]

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