Ethylmagnesium bromide

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

Ethylmagnesium bromide

Identifiers
CAS Number	925-90-6 Y
3D model (JSmol)	Interactive image
ChemSpider	10254342 Y
ECHA InfoCard	100.011.935
PubChem CID	101914
UNII	5564378HK3 Y
CompTox Dashboard (EPA)	DTXSID80275976
InChI InChI=1S/C2H5.BrH.Mg/c1-2;;/h1H2,2H3;1H;/q;;+1/p-1 Y Key: TWTWFMUQSOFTRN-UHFFFAOYSA-M Y 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). Y verify (what is YN ?) Infobox references

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:

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:

EtBr + Mg → EtMgBr