Phenylmagnesium bromide is a strong nucleophile as well as a strong base. The compound invariably forms an adduct with two OR2 ligands from the ether or THF solvent. Phenylmagnesium bromide, with the simplified formula C6H5MgBr, is a magnesium-containing organometallic compound. 100-58-3 - ANRQGKOBLBYXFM-UHFFFAOYSA-M - Phenylmagnesium bromide - Similar structures search, synonyms, formulas, resource links, and other chemical information. Dès que la réaction s'amorce, l'éther se colore en gris-violet et la solution s'échauffe jusqu'à ébullition au fur et à mesure que l'on verse du bromobenzène. Laboratory preparation involves treating bromobenzene with magnesium metal, usually in the form of turnings. Thus the Mg is tetrahedral and obeys the octet rule. © 1997-2020 LUMITOS AG, All rights reserved, https://www.chemeurope.com/en/encyclopedia/Phenylmagnesium_bromide.html, Your browser is not current. In order prevent decomposition of the Grignard reagent it will be used immediately in the solution that it is in; there is no isolation or purification of the phenylmagnesium bromide. Coordinating solvents such as ether or THF, are required to solvate (complex) the magnesium(II) center. Although phenylmagnesium bromide is routinely represented as C 6 H 5 MgBr, the molecule is more complex.The compound invariably forms an adduct with two OR 2 ligands from the ether or THF solvent. La dernière modification de cette page a été faite le 31 octobre 2018 à 22:30. Although phenylmagnesium bromide is routinely represented as C6H5MgBr, the molecule is more complex. The compound invariably forms an adduct with two OR 2 ligands from the ether or THF solvent. Carbonyl-containing solvents, such as acetone and ethyl acetate, are also incompatible with the reagent. Predicted data is generated using the ACD/Labs Percepta Platform – PhysChem Module. Il est utilisé en synthèse organique pour introduire le synthon phényle « Ph– ». Accessed 28 Oct 2006. Thus, the Mg is tetrahedral and obeys the octet rule. Advanced Search | Structure Search Phenylmagnesium bromide solution ... 3,5-Bis(trifluoromethyl) phenylmagnesium bromide solution. A small amount of iodine may be used to activate the magnesium by removing the oxide surface. It often adds to carbonyls, which are electron-deficient, such as in the laboratory synthesis of benzoic acid and triphenylmethanol. Phenylmagnesium bromide is a Grignard reagent. A polar solvent is required to solvate the magnesium portion of the molecule, hence the use of ether or THF. Il forme généralement des composés d'addition avec les carbonyles tels que les cétones et les aldéhydes. Phenylmagnesium bromide can be prepared in the laboratory by treating bromobenzene with magnesium metal, usually in the form of ribbon. Click to predict properties on the Chemicalize site, We use cookies to give you the best experience possible. Cet halogénure organomagnésien, analogue bromé du chlorure de phénylmagnésium, est un réactif de Grignard dérivé du benzène disponible dans le commerce, généralement dissous dans l'éther diéthylique ou dans le THF. Phenylmagnesium bromide | C6H5BrMg | CID 66852 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. [1][3] With carbon dioxide, it reacts to give benzoic acid after an acidic workup. To use all functions of this page, please activate cookies in your browser. Phenylmagnesium bromide can be prepared in the laboratory by treating bromobenzene with magnesium metal, usually in the form of ribbon. Phenylmagnesium bromide solution 3.0 M in diethyl ether, https://fr.wikipedia.org/w/index.php?title=Bromure_de_phénylmagnésium&oldid=153561631, Infobox Chimie avec données 67/548/EEC redondantes à supprimer, licence Creative Commons attribution, partage dans les mêmes conditions, comment citer les auteurs et mentionner la licence. Read what you need to know about our industry portal chemeurope.com. A polar solvent is required to solvate the magnesium portion of the molecule, hence the use of ether or THF. * Please contact us if you need further information. The Mg–O distances are 201 and 206 pm whereas the Mg–C and Mg–Br distances are 220 pm and 244 pm, respectively.[2]. phenylmagnesium bromide CAS Number: 100-58-3: Molecular Weight: 181.313: Density: 1.134 g/mL at 25 °C: Boiling Point: 78.8ºC at 760 mmHg: Molecular Formula: C 6 H 5 BrMg: Melting Point: N/A: MSDS: Chinese: Flash Point −40 °F: Symbol: GHS02, GHS05, GHS07: Signal Word: Danger × Preparation and structure. Thus, the Mg is tetrahedral and obeys the octet rule. phenylmagnesium bromide C6H5BrMg structure, (2-Methoxy-2-oxoethyl)(triphenyl)phosphonium bromide C21H20BrO2P structure, Benzyl triphenyl phosphonium bromide C25H22BrP structure, Free online plagiarism checker with percentage, P210-P231+P232-P303+P361+P353-P305+P351+P338-P405-P501a, P210-P260-P303+P361+P353-P305+P351+P338-P405-P501a. The reaction is complete when none of the magnesium remains. Thus, the Mg is tetrahedral and obeys the octet rule. Your browser does not support JavaScript. Phenylmagnesium bromide, with the simplified formula C6H5MgBr, is a magnesium-containing organometallic compound. Un article de Wikipédia, l'encyclopédie libre. It is often used as a synthetic equivalent for the "Ph−" phenyl synthon. La structure du bromure de phénylmagnésium en solution est plus complexe que ne le laisse penser la formule C6H5MgBr, car l'atome de magnésium forme un adduit avec deux atomes d'oxygène de deux molécules de solvant, éther diéthylique (C2H5)2O ou THF (CH2)4O par exemple. By continuing we’ll assume you’re on board with our cookie policy. InChI=1S/C6H5.BrH.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q;;+1/p-1, InChI=1/C6H5.BrH.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q;;+1/p-1/rC6H5BrMg/c7-8-6-4-2-1-3-5-6/h1-5H, Except where otherwise noted, data are given for materials in their, Phenylmagnesium bromide is prepared by reaction of, CS1 maint: multiple names: authors list (, "Grignard Synthesis: Synthesis of Benzoic Acid and of Triphenylmethanol". It is often used as a synthetic equivalent for the phenyl "Ph−" synthon. With an accout for my.chemeurope.com you can always see everything at a glance – and you can configure your own website and individual newsletter. Find out more about the company LUMITOS and our team. The solvent must be aprotic since alcohols and water contain an acidic proton and thus react with phenylmagnesium bromide to give benzene. Il est capable d'absorber des protons même relativement acides. Oxford University, Phenylmagnesium bromide in ether, Aug 19 2005. Categories: Organometallic compounds | Magnesium compounds. Le bromure de phénylmagnésium est un composé chimique de formule C6H5MgBr. COVID-19 is an emerging, rapidly evolving situation. Le bromure de phénylmagnésium obtenu n'est pas purifié mais, comme le sont généralement les réactifs de Grignard, est utilisé en solution. phenylmagnesium bromide. The solvent must be aprotic since alcohols and water contain an acidic proton and thus react with phenylmagnesium bromide to give benzene. On utilise des solvants aprotiques — car les alcools et l'eau contiennent des protons acides qui réagissent avec le soluté pour donner du benzène C6H6 — et complexants, tels que le tétrahydrofurane (THF) afin de solvater l'atome de magnésium. It often adds to carbonyls, such as ketones, aldehydes. If three equivalents are reacted with phosphorus trichloride, triphenylphosphine can be made. Phenylmagnesium bromide is commercially available as solutions of diethyl ether or THF. A small amount of iodine may be used to activate the magnesium to initiate the reaction.[1]. La longueur de la liaison Mg–O est de 201 pm et 206 pm, celle de la liaison Mg–C vaut 220 pm et celle de la liaison Mg–Br vaut 244 pm[3]. Molecular Formula C 6 H 5 BrMg; Average mass 181.313 Da; Monoisotopic mass 179.942490 Da; ChemSpider ID 10254417 1mol/L) (CAS RN:100-58-3 Product Number:P2025) Structure. It is commercially available as a solution in diethyl ether or tetrahydrofuran (THF). It often adds to carbonyls, such as ketones, aldehydes. Le bromure de phénylmagnésium est un composé chimique de formule C6H5MgBr.

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