| Revision as of 20:19, 12 April 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - updated 'UNII_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemica← Previous edit |
Latest revision as of 23:10, 30 July 2024 edit undoDMacks (talk | contribs)Edit filter managers, Autopatrolled, Administrators186,375 edits →Reactions: BuLi is used as the base not EtMgBr, it's deprotonating at the propargylic position not the alkyne itself (though this would be a novel use worth mentioning if EtMgBr were involved). the only ethyl is EtBr as electrophile. |
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{{chembox |
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{{chembox |
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| verifiedrevid = 396488078 |
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| verifiedrevid = 423740839 |
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|ImageFile=Ethylmagnesium bromide.png |
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| ImageFile=Ethylmagnesiumbromide-Structural Formula V.svg |
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|ImageSize=150px |
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| ImageSize=150px |
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|IUPACName= |
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|OtherNames= |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10254342 |
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| ChemSpiderID = 10254342 |
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| InChI = 1/C2H5.BrH.Mg/c1-2;;/h1H2,2H3;1H;/q;;+1/p-1/rC2H5BrMg/c1-2-4-3/h2H2,1H3 |
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| InChI = 1/C2H5.BrH.Mg/c1-2;;/h1H2,2H3;1H;/q;;+1/p-1/rC2H5BrMg/c1-2-4-3/h2H2,1H3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=925-90-6 |
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| CASNo=925-90-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=101914 |
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| SMILES = BrCC |
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| UNII = 5564378HK3 |
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| PubChem=101914 |
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| SMILES = BrCC |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C = 2 | H = 5 | Mg = 1 | Br = 1 |
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| C=2 | H=5 | Mg=1 | Br=1 |
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'''Ethylmagnesium bromide''' is a ] with formula C<sub>2</sub>H<sub>5</sub>MgBr or C<sub>2</sub>H<sub>5</sub>Mg<sup>+</sup>·Br<sup>−</sup>, namely a ] ion with a ] to an ] ] and an ] to a ] anion. It is widely used in the laboratory synthesis of ]s. |
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'''Ethylmagnesium bromide''' is a ] with formula C<sub>2</sub>H<sub>5</sub>MgBr. It is widely used in the laboratory synthesis of ]s. |
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==Reactions== |
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== Reactions == |
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Apart from acting as the ] of an ethyl anion ] for ], ethylmagnesium bromide may be used as a strong base to deprotonate various substrates such as ]s:<ref> |
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Apart from acting as the ] of an ethyl anion ] for ], ethylmagnesium bromide may be used as a strong base to deprotonate various substrates such as ]s:<ref>{{OrgSynth | author = Quillinan, A. J. | author2 = Scheinmann, F. | title = 3-Alkyl-1-alkynes Synthesis: 3-Ethyle-1-hexyne | year = 1978 | volume = 58 | pages = 1 | collvol = 6 | collvolpages = 595 | prep = cv6p0595}}</ref><!--double deprotonation of hexyne followed by ethylation--> |
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{{OrgSynth | author = Taniguchi, H.; Mathai, I. M.; Miller, S. I. | title = 1-Phenyl-1,4-Pentadiyne and 1-Phenyl-1,3-Pentadiyne | volume = 50 | pages = 97 | collvol = 6 | collvolpages = 925 | prep = cv6p0925}} |
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</ref><ref> |
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{{OrgSynth | author = A. J. Quillinan, A. J.; Scheinmann, F. | title = 3-Alkyl-1-alkynes Synthesis: 3-Ethyle-1-hexyne | volume = 58 | pages = 1 | collvol = 6 | collvolpages = 595 | prep = cv6p0595}} |
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</ref><!--double deprotonation of hexyne followed by ethylation--><ref> |
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{{OrgSynth | author = Newman, M. S.; Stalick, W. M. | title = 1-Ethoxy-1-butyne | volume = 57 | pages = 65 | collvol = 6 | collvolpages = 564 | prep = cv6p0564}}</ref><!--ethylation of acetylide--> |
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:RC≡CH + EtMgBr → RC≡CMgBr + ] |
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:RC≡CH + EtMgBr → RC≡CMgBr + ] |
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In this application, ethylmagnesium bromide has been supplanted by the wide availability of ]s. |
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In this application, ethylmagnesium bromide has been supplanted by the wide availability of ]s. |
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==Preparation== |
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==Preparation== |
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Ethylmagnesium bromide is commercially available, usually as a solution in ] or ]. It may be prepared in the normal manner of ]s — by reacting ] with ] in ]:<ref>{{OrgSynth | title = Triethyl Carbinol | author = W. W. Moyer and C. S. Marvel | collvol = 2 | collvolpages = 602 | prep = cv2p0602}}</ref> |
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Ethylmagnesium bromide is commercially available, usually as a solution in ] or ]. It may be prepared in the normal manner of ]s — by reacting ] with ] in ]:<ref>{{ OrgSynth | author = Moyer, W. W. | author2 = Marvel, C. S. | title = Triethyl Carbinol | year = 1931 | volume = 11 | pages = 98 | collvol = 2 | collvolpages = 602 | prep = cv2p0602 }}</ref> |
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:EtBr + Mg → EtMgBr |
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:EtBr + Mg → EtMgBr |
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==References== |
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==References== |
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{{Reflist}} |
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<References/> |
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] |
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