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;
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 (SDS)	Oxford MSDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.

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

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