Ethylmagnesium bromide solution

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Ethylmagnesium Bromide Solution (C₂H₅MgBr)

Ethylmagnesium bromide (C₂H₅MgBr) is an organomagnesium compound and a type of Grignard reagent. It is commonly used in organic chemistry for carbon-carbon bond formation reactions, specifically in the synthesis of alcohols, aldehydes, and ketones. Ethylmagnesium bromide is typically handled as a solution in anhydrous ether or THF (tetrahydrofuran), as it is highly reactive and moisture-sensitive.

Key Characteristics:

Chemical Formula: C₂H₅MgBr

Appearance: Typically, the solution is clear and colorless but may be pale yellow or cloudy due to impurities or air exposure.

Solvent: Usually dissolved in anhydrous ether (like diethyl ether) or THF (tetrahydrofuran).

Reactivity: It is highly reactive with moisture and oxygen, so it must be handled in an anhydrous (dry) environment, often under inert atmosphere conditions such as nitrogen or argon.

Properties of Ethylmagnesium Bromide Solution:

Solubility: It is highly soluble in dry ether and tetrahydrofuran but reacts rapidly with water and moisture.

Basicity: As a Grignard reagent, it is a strong nucleophile and a strong base.

Decomposition: Reacts violently with water to form ethane (C₂H₆), magnesium hydroxide, and the corresponding alcohol.

$C2H5MgBr+H2O→C2H6+Mg(OH)2+HBrtext{C}_2text{H}_5text{MgBr} + text{H}_2text{O} rightarrow text{C}_2text{H}_6 + text{Mg(OH)}_2 + text{HBr}$

Reactivity with Carbonyl Compounds: Ethylmagnesium bromide is typically used to form alcohols by reacting with carbonyl compounds (like aldehydes and ketones).

$C2H5MgBr+RCHO→RCH(OH)C2H5text{C}_2text{H}_5text{MgBr} + text{RCHO} rightarrow text{RCH(OH)C}_2text{H}_5$

Formation of Grignard Reagents: Ethylmagnesium bromide is one of the most common Grignard reagents, often synthesized by reacting magnesium metal with ethyl bromide in dry ether.

$etherC2H5MgBrtext{C}_2text{H}_5text{Br} + text{Mg} xrightarrow{text{dry ether}} text{C}_2text{H}_5text{MgBr}$

Applications:

Synthesis of Alcohols: Ethylmagnesium bromide is frequently used in reactions where it adds to carbonyl compounds (such as aldehydes or ketones) to form secondary or tertiary alcohols.

Formation of C-C Bonds: Grignard reagents, including ethylmagnesium bromide, are used in many carbon-carbon bond-forming reactions, making them essential in organic synthesis.

Preparation of Organometallic Compounds: Used to synthesize a variety of other organomagnesium compounds, as well as for the preparation of complex organometallic intermediates.

Synthetic Chemistry: It plays a role in a broad range of synthetic reactions, including nucleophilic additions, reductions, and other complex organic transformations.

Safety and Handling:

Highly Reactive: Ethylmagnesium bromide is extremely reactive with water, air, and moisture. It can cause fires or violent reactions if it comes into contact with moisture.

Toxicity: It can be toxic if inhaled or ingested and should not come into contact with the skin or eyes.

Protective Measures: Use gloves, goggles, and appropriate protective clothing when handling this reagent. Always work in a fume hood and under an inert atmosphere (e.g., nitrogen or argon) to avoid contact with moisture and oxygen.

Disposal: Grignard reagents should be disposed of by quenching with dry, ice-cold water in a fume hood to safely neutralize the chemical.

Where to Buy Ethylmagnesium Bromide Solution:

Ethylmagnesium bromide solution can be purchased from a number of chemical supply companies, often available in standard concentrations (e.g., 1 M or 3 M in anhydrous ether or THF). Some reputable suppliers include:

Sigma-Aldrich (Merck)

Fisher Scientific

VWR

Alfa Aesar

TCI Chemicals

Storage:

Storage Conditions: Store under inert conditions, such as in a sealed container flushed with nitrogen or argon, in a dry and cool place.

Shelf Life: The shelf life may vary depending on the solution’s concentration and the solvent used. It’s recommended to use it as soon as possible after delivery for optimal performance in reactions.

Conclusion:

Ethylmagnesium bromide is an important Grignard reagent widely used in organic synthesis, especially for carbon-carbon bond formation reactions. It is highly reactive and must be handled with extreme care under dry conditions. If you need a specific concentration or solution, many chemical supply companies offer it in various forms. Always check product safety data sheets and supplier details before use to ensure safe and appropriate handling.

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ETHYLMAGNESIUM BROMIDE SOLUTION

Ethylmagnesium bromide solution