Ethylmagnesium bromide

Ethylmagnesium bromide
Identifiers
CAS Number	925-90-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	10254342 ;
ECHA InfoCard	100.011.935
PubChem CID	101914;
UNII	5564378HK3 ;
CompTox Dashboard (EPA)	DTXSID80275976 ;
	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	133.271 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. 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

Taniguchi, H.; Mathai, I. M.; Miller, S. I. (1970). "1-Phenyl-1,4-Pentadiyne and 1-Phenyl-1,3-Pentadiyne". Organic Syntheses. 50: 97.CS1 maint: multiple names: authors list (link); Collective Volume, 6, p. 925
Quillinan, A. J.; Scheinmann, F. (1978). "3-Alkyl-1-alkynes Synthesis: 3-Ethyle-1-hexyne". Organic Syntheses. 58: 1.CS1 maint: multiple names: authors list (link); Collective Volume, 6, p. 595
Newman, M. S.; Stalick, W. M. (1977). "1-Ethoxy-1-butyne". Organic Syntheses. 57: 65.CS1 maint: multiple names: authors list (link); Collective Volume, 6, p. 564
Moyer, W. W.; Marvel, C. S. (1931). "Triethyl Carbinol". Organic Syntheses. 11: 98.CS1 maint: multiple names: authors list (link); Collective Volume, 2, p. 602

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[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.CS1 maint: multiple names: authors list (link); Collective Volume, 6, p. 925

[2] Quillinan, A. J.; Scheinmann, F. (1978). "3-Alkyl-1-alkynes Synthesis: 3-Ethyle-1-hexyne". Organic Syntheses. 58: 1.CS1 maint: multiple names: authors list (link); Collective Volume, 6, p. 595

[3] Newman, M. S.; Stalick, W. M. (1977). "1-Ethoxy-1-butyne". Organic Syntheses. 57: 65.CS1 maint: multiple names: authors list (link); Collective Volume, 6, p. 564

[4] Moyer, W. W.; Marvel, C. S. (1931). "Triethyl Carbinol". Organic Syntheses. 11: 98.CS1 maint: multiple names: authors list (link); Collective Volume, 2, p. 602