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Ethylmagnesium Bromide CAS 925-90-6

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  • Appearance: Pale yellow to brown solution
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: Ethylmagnesium Bromide Supplement

Basic Info of Ethylmagnesium Bromide

What is Ethylmagnesium Bromide?

Ethylmagnesium bromide, molecular formula: C2H5MgBr, prepared by the response of steel magnesium and bromoethane in anhydrous ether. The relative density of commercial product (ether solution) is about 1.01. for Grignard reaction. Similar is ethyl magnesium chloride, which is a solution of ether or tetrahydrofuran with a relative density of 0.85.

Ethylmagnesium bromide is generally present and used in solution. Soluble in ether, butyl ether, isopropyl ether, THF and anisole.

It is sold by international large-scale reagent companies, and can also be directly prepared by reacting bromoethane with magnesium powder or magnesium chips in anhydrous ether.

Ethylmagnesium bromide is moisture sensitive and is prepared and used in dry systems.

Ethylmagnesium Bromide Uses

  1. Ethylmagnesium bromide solution (3.0 M in ether) can be utilized for copper(I)-militarized allylic alternative responses.
  2. Ethylmagnesium bromide is an organomagnesium compound, commonly known as Grignard reagent.It is a powerful carbon nucleophilic reagent, which is mainly used to form CC bond.
  3. Ethylmagnesium bromide is a useful reagent for preparing zirconium complexes with two phenoxyimine chelating ligands for olefin polymerization.
  4. Ethyl magnesium bromide is commercially available and is usually used as a solution in ether or tetrahydrofuran.

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Commonly Used Organometallic Reagents---Ethylmagnesium Bromide

Reaction with carbonyl compounds Ethylmagnesium bromide reacts with aldehydes to give secondary alcohols. Various aliphatic, aromatic (Formula 1) and allyl aldehydes can be converted into the corresponding hydroxy derivatives.

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Addition of EtMgBr to ketones produces tertiary alcohols. The stereoselectivity of this addition reaction depends on the ketone structure, solvent, reaction temperature and stereoselective activator. In the presence of Ti(OPr-i)4, EtMgBr reacts with acetophenone to form pinacol (Formula 2).

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Typically, Grignard reagents react with esters to give tertiary alcohols (formates give secondary alcohols). In the presence of Ti(OPr-i)4, esters react with EtMgBr to give ternary cyclic compounds (Formula 3).

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Ethyl ketone can be obtained by the action of acid chloride with EtMgBr. In the presence of indole, EtMgBr can promote the acylation of acid chloride on the 3-carbon of indole (Formula 4).

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Reaction with carbon-carbon and carbon-nitrogen unsaturated bonds EtMgBr can act as a base and react with acidic terminal 

alkyne hydrogens, and the formed alkyne carbanion participates in the reaction as a nucleophile (Formula 5).

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EtMgBr reacts with cyano group to obtain ethyl ketone (formula 6), but the yield is low.

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EtMgBr can react with iodine-substituted imidazole ring, remove iodine to form carbanion, and then carry out nucleophilic addition with aldehyde and ketone (Formula 7). In the presence of cuprous iodide, the ethyl group of EtMgBr can also replace iodine to form an alkyne bond (Formula 8).

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Under the action of catalyst, EtMgBr can undergo 1,4-asymmetric addition with α,β-unsaturated ketone or lactone to form asymmetric β-ketone.

Interaction with sulfur atoms EtMgBr can easily attack and sever the S-S bond of the 1,2-dithiolane ring.

Reaction of EtMgBr with a thiothiol ester yields the thioacetal (Formula 9).

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Reference

  1. Ethylmagnesium Bromide – PubChem
  2. Ooi, T.; Takeuchi, M.; Kato, D.; Uematsu, Y.; Tayama, E.; Sakai, D.; Maruoka, K- J. Am. Chem. Soc.2005,127, 5073
  3. Kelly, B. G.; Gilheany, D. G. Tetrahedron Lett. 2002,431 887.

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