925-90-6 Usage
Description
Ethylmagnesium bromide, also known as a Grignard reagent, is an organomagnesium compound that serves as a powerful carbon nucleophile. It is commonly used for C-C bond formation and is typically sold as a dark brown solution. ETHYLMAGNESIUM BROMIDE can be dissolved in various anhydrous solvents such as diethyl ether, butyl ether, isopropyl ether, THF, and anisole. Grignard reagents, including ethylmagnesium bromide, were discovered by French chemist Victor Grignard in 1900 and have since been widely used in organic synthesis.
Uses
Used in Chemical Synthesis:
Ethylmagnesium bromide is used as a reagent for the preparation of zirconium complexes that have two phenoxy-imine chelate ligands. These complexes are essential for olefin polymerization, a process that produces polymers with a wide range of applications in various industries.
Used in Organic Synthesis:
As a Grignard reagent, ethylmagnesium bromide is used as a carbon nucleophile for C-C bond formation in organic synthesis. This application is crucial for the creation of various organic compounds and contributes to the development of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Copper(I)-Catalyzed Allylic Substitution Reaction:
Ethylmagnesium bromide solution (3.0 M in diethyl ether) is utilized in copper(I)-catalyzed allylic substitution reactions. This reaction is an important method in organic chemistry for the formation of carbon-carbon and carbon-heteroatom bonds, which are vital for the synthesis of complex organic molecules.
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
Reactions
Ethylmagnesium bromide reacts with water to produce ethane.CH3CH2MgBr+H2O→CH3-CH3+Mg(OH)BrReaction of ethylmagnesium bromide with ethyl acetate in the presence of styrene and titanium(IV) isopropoxide as a catalyst leads to (Z)-1-methyl-2-phenylcyclopropanol in 42% yield.
Hazard
Flammable, dangerous fire risk.
Check Digit Verification of cas no
The CAS Registry Mumber 925-90-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,2 and 5 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 925-90:
(5*9)+(4*2)+(3*5)+(2*9)+(1*0)=86
86 % 10 = 6
So 925-90-6 is a valid CAS Registry Number.
InChI:InChI=1/C2H5.BrH.Mg/c1-2;;/h1H2,2H3;1H;/q;;+1/p-1/rC2H5BrMg/c1-2-4-3/h2H2,1H3
925-90-6Relevant articles and documents
Synthesis and structures of titanium complexes bearing tetradentate tripodal [O2XC] ligands (X = C, P)
Nakanishi, Yusuke,Ishida, Yutaka,Kawaguchi, Hiroyuki
, p. 27 - 30 (2019)
We report the synthesis and structures of titanium complexes supported by tripodal mixed-donor [O2CC] and [O2PC] ligands. Stepwise cyclometallation of a chelating bis(phenoxide) complex led to tetradentate binding of the [O2CC] ligand to the titanium center. Phosphination of a Ti-C bond of the [O2CC] complex afforded the tripodal [O2PC] ligand.
Scalable Continuous Synthesis of Grignard Reagents from in Situ-Activated Magnesium Metal
Deitmann, Eva,G?ssl, Lars,Hofmann, Christian,L?b, Patrick,Menges-Flanagan, Gabriele
, p. 315 - 321 (2020/03/10)
The continuous synthesis of Grignard reagents has been investigated under continuous processing conditions using Mg turnings at variable liquid throughputs and concentrations. A novel process window easily accessible through continuous processing was employed, namely, using a large molar access of Mg turnings within the reactor and achieving Mg activation by mechanical means. A laboratory and a 10-fold-increased pilot-scale reactor setup were built and evaluated, including integrated inline analytics via ATR-IR measurements. The main goal of this work was to explore the full potential of classic Grignard reagent formation through the use of scalable flow chemistry and to allow for fast and safe process optimization. It was found that on both the laboratory and pilot scales, full conversion of the employed halides could be achieved with a single passage through the reactor. Furthermore, Grignard reagent yields of 89-100% were reached on the laboratory scale.
Ni-Catalyzed β-Alkylation of Cyclopropanol-Derived Homoenolates
Mills, L. Reginald,Zhou, Cuihan,Fung, Emily,Rousseaux, Sophie A. L.
supporting information, p. 8805 - 8809 (2019/11/03)
Metal homoenolates are valuable synthetic intermediates which provide access to β-functionalized ketones. In this report, we disclose a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived homoenolates using redox-active N-hydroxyphthalimide (NHPI) esters as the alkylating reagents. The reaction is compatible with 1°, 2°, and 3° NHPI esters. Mechanistic studies imply radical activation of the NHPI ester and 2e β-carbon elimination occurring on the cyclopropanol.