Ethylmagnesium bromide

Ethylmagnesium bromide

Identifiers
CAS Number	925-90-6
ChemSpider	10254342
Jmol interactive 3D	Image
PubChem	101914
InChI InChI=1S/C2H5.BrH.Mg/c1-2;;/h1H2,2H3;1H;/q;;+1/p-1 Key: TWTWFMUQSOFTRN-UHFFFAOYSA-M InChI=1/C2H5.BrH.Mg/c1-2;;/h1H2,2H3;1H;/q;;+1/p-1/rC2H5BrMg/c1-2-4-3/h2H2,1H3 Key: TWTWFMUQSOFTRN-QJSJVVHYAJ
SMILES Br[Mg]CC
Properties
Chemical formula	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

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". 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