Vinylmagnesium chloride
[CAS# 3536-96-7]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organomagnesium
• Name: Vinylmagnesium chloride
• Molecular Formula: C₂H₃ClMg
• Molecular Weight: 86.80
• CAS Registry Number: 3536-96-7
• EC Number: 222-575-9
• SMILES: C=[CH-].[Mg+2].[Cl-]

Properties

• Density: 0.975
• Boiling point: 66 °C
• Flash point: -17 °C
• Water solubility: vigorous reaction

Safety Data

• Hazard Symbols: GHS02;GHS05 Danger
• Risk Statements: H225-H260-H314-H318
• Safety Statements: P210-P223-P231+P232-P233-P240-P241-P242-P243-P260-P264-P264+P265-P280-P301+P330+P331-P302+P335+P334-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P317-P321-P363-P370+P378-P402+P404-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Substances or mixtures which in contact with water emit flammable gases	Water-react.	1	H260
Flammable liquids	Flam. Liq.	2	H225
Serious eye damage	Eye Dam.	1	H318

Discovery and Applications

Vinyl magnesium chloride (VMC) is a highly reactive organomagnesium compound with the molecular formula C₂H₃MgCl. It is an essential reagent in organic synthesis and is particularly valued for its role in forming carbon-carbon bonds.

Vinyl magnesium chloride was first synthesized in the early 20th century as an attempt to expand the utility of Grignard reagents. These reagents, named after the French chemist Victor Grignard, revolutionized organic synthesis by forming complex organic molecules. Vinyl magnesium chloride is characterized by a vinyl (vinyl) group bound to the magnesium atom, which is further coordinated to a chloride ion.

The compound is typically prepared by reacting vinyl chloride with magnesium metal in anhydrous ether. The reaction is highly exothermic and needs to be carefully controlled to prevent decomposition. Vinyl magnesium chloride is a colorless to pale yellow liquid that is highly reactive, especially with water and air, and must therefore be stored under inert gas.

Vinyl magnesium chloride is used to form carbon-carbon bonds via nucleophilic addition reactions. It reacts with a variety of electrophiles, such as carbonyl compounds, to produce β-hydroxyalkyl compounds or other functionalized products. This reaction is essential for the synthesis of complex molecules, including drugs and natural products.

VMC is used to introduce vinyl groups into organic molecules. This application is important for the preparation of vinyl ethers, esters, and other vinyl-substituted derivatives, which are key intermediates in organic synthesis.

Vinyl magnesium chloride can react with a variety of electrophiles, such as aryl halides or other alkyl halides, in cross-coupling reactions to form biaryls or other complex structures. These reactions are essential for the construction of complex organic frameworks for drug development and materials science.

VMC is used for the polymerization of vinyl-containing monomers. This process results in the formation of polymers with specific vinyl functional groups, which are very useful for the manufacture of specialized materials and coatings.

Due to its high reactivity, vinyl magnesium chloride must be handled with extreme caution. It is extremely flammable and reacts violently with water and air, producing flammable gases and heat. Therefore, it should be handled in a well-ventilated fume hood and with appropriate protective equipment, including gloves and goggles. It should be stored in a closed container under an inert gas, usually nitrogen or argon.

References

2020. Vinyl Grignard Reagents in Synthesis. Synlett, 31(15).
DOI: 10.1055/s-0040-1707123