Methylmagnesium chloride
[CAS# 676-58-4]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organomagnesium
• Name: Methylmagnesium chloride
• Molecular Formula: CH₃ClMg
• Molecular Weight: 74.79
• CAS Registry Number: 676-58-4
• EC Number: 211-629-7
• SMILES: [CH3-].[Mg+2].[Cl-]

Properties

• Density: 1.013
• Boiling point: 66 ºC
• Flash point: -17 ºC
• Water solubility: reacts

Safety Data

• Hazard Symbols: GHS02;GHS05 Danger
• Hazard Statements: H225-H250-H260-H21-H314-H318
• Precautionary Statements: P210-P222-P223-P231-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
Pyrophoric liquids	Pyr. Liq.	1	H250
Serious eye damage	Eye Dam.	1	H318
Flammable liquids	Flam. Liq.	2	H225
Specific target organ toxicity - single exposure	STOT SE	3	H335
Substances or mixtures which in contact with water emit flammable gases	Water-react.	2	H261
Carcinogenicity	Carc.	2	H351
Flammable liquids	Flam. Liq.	1	H224
Flammable liquids	Flam. Liq.	3	H226

• Transport Information: UN 3399

Discovory and Applicatios

Methylmagnesium chloride (CH₃MgCl) is an important organomagnesium compound and a member of the Grignard family of reagents that plays an important role in organic synthesis. Its ability to form carbon-carbon bonds has made it a cornerstone of modern chemical research and industry.

Methylmagnesium chloride was first synthesized in the early 20th century following the discovery of Grignard reagents by Victor Grignard, who won the Nobel Prize in Chemistry in 1912. Grignard's work revolutionized organic chemistry by providing a method to form carbon-carbon bonds in a variety of chemical transformations.

Methylmagnesium chloride is typically prepared by reacting methyl chloride (CH₃Cl) with magnesium metal (Mg) in anhydrous diethyl ether. The reaction is exothermic and requires careful handling to avoid side reactions. The resulting compound is a colorless to pale yellow liquid with a strong and distinctive odor. It is highly reactive and must be stored under inert conditions away from moisture and air.

Methylmagnesium chloride is primarily used to form carbon-carbon bonds via nucleophilic addition reactions. It reacts with various electrophiles such as carbonyl compounds to form alcohols. For example, it reacts with aldehydes and ketones to form secondary and tertiary alcohols, respectively.

This compound is essential for the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and natural products. It facilitates the construction of complex molecular frameworks by adding methyl groups to different chemical structures.

Methylmagnesium chloride is used to methylate a variety of substrates, including acids, esters, and amides. This methylation is important for changing the chemical properties of compounds, affecting their reactivity and biological activity.

Methylmagnesium chloride, combined with other Grignard reagents, participates in cross-coupling reactions to form a variety of organic compounds. These reactions are critical for building complex molecules in pharmaceutical and material sciences.

Due to its high reactivity, methylmagnesium chloride must be handled with extreme caution. It is extremely flammable and reacts violently with water and air, producing flammable gases and heat. It should be stored in a dry, inert environment, such as nitrogen or argon, and handled in a well-ventilated fume hood with appropriate protective equipment, including gloves and goggles.