Chemistry:Ethylmagnesium bromide
From HandWiki
| |
| Identifiers | |
|---|---|
3D model (JSmol)
|
|
| ChemSpider | |
PubChem CID
|
|
| UNII | |
| |
| |
| Properties | |
| 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). | |
 verify (what is   ?)
| |
| Infobox references | |
Tracking categories (test):
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. http://www.orgsyn.org/demo.aspx?prep=cv6p0925.; Collective Volume, 6, pp. 925
- ↑ Quillinan, A. J.; Scheinmann, F. (1978). "3-Alkyl-1-alkynes Synthesis: 3-Ethyle-1-hexyne". Organic Syntheses 58: 1. http://www.orgsyn.org/demo.aspx?prep=cv6p0595.; Collective Volume, 6, pp. 595
- ↑ Newman, M. S.; Stalick, W. M. (1977). "1-Ethoxy-1-butyne". Organic Syntheses 57: 65. http://www.orgsyn.org/demo.aspx?prep=cv6p0564.; Collective Volume, 6, pp. 564
- ↑ Moyer, W. W.; Marvel, C. S. (1931). "Triethyl Carbinol". Organic Syntheses 11: 98. http://www.orgsyn.org/demo.aspx?prep=cv2p0602.; Collective Volume, 2, pp. 602
 |  |
