Isopropylmagnesium chloride
[CAS# 1068-55-9]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organomagnesium
• Name: Isopropylmagnesium chloride
• Synonyms: Chloro(1-methylethyl)magnesium
• Molecular Formula: C₃H₇ClMg
• Molecular Weight: 102.85
• CAS Registry Number: 1068-55-9
• EC Number: 213-947-1
• SMILES: C[CH-]C.[Mg+2].[Cl-]

Properties

• Density: 0.834
• Flash point: -17 °C

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

• Transport Information: UN 3399

Discovery and Applications

Isopropylmagnesium chloride, with the formula (CH₃)₂CHMgCl, is an organomagnesium compound that belongs to the class of Grignard reagents. These reagents are used in organic chemistry to form carbon-carbon bonds, particularly in various organic synthesis processes.

Grignard reagents were first discovered by French chemist François Auguste Victor Grignard in 1900, for which he was awarded the Nobel Prize in Chemistry in 1912. The preparation of isopropylmagnesium chloride typically involves the reaction of isopropyl chloride with magnesium metal in an anhydrous ether solvent such as diethyl ether or tetrahydrofuran (THF). The process is highly sensitive to moisture and requires strict anhydrous conditions to prevent the reagent from decomposing.

Isopropylmagnesium chloride is a colorless to pale yellow solution when dissolved in diethyl ether. It is highly reactive and acts as a strong nucleophile and base. The reagent is very useful in forming carbon-carbon bonds due to the high reactivity of the magnesium-carbon bond, which reacts with various electrophiles, including carbonyl compounds, to form alcohols, acids, and other derivatives.

Isopropylmagnesium chloride is widely used in organic synthesis to produce complex molecules. Its main application is the formation of alcohols by adding isopropyl groups to carbonyl compounds such as aldehydes and ketones. This reaction is called the Grignard reaction and is fundamental to synthetic organic chemistry.

For example, when isopropylmagnesium chloride reacts with formaldehyde, it produces isopropyl alcohol, an important industrial alcohol. When it reacts with acetone, it forms 2-methyl-2-butanol, a valuable intermediate for pharmaceuticals and agrochemicals.

In the pharmaceutical industry, isopropylmagnesium chloride is used to synthesize a variety of active pharmaceutical ingredients (APIs). It is essential for the development of new drugs because of its ability to efficiently form carbon-carbon bonds and introduce isopropyl groups into complex molecules. For example, it can be used to synthesize steroid drugs, where the introduction of specific alkyl groups is essential for biological activity.

Because isopropylmagnesium chloride is highly reactive, it must be handled with care. It is pyrophoric, meaning it will spontaneously ignite when exposed to air. Proper storage under an inert gas such as nitrogen or argon is essential. In addition, it can react violently with water, producing flammable gases. Personal protective equipment such as gloves and goggles should always be used when handling this reagent.

References

2024. Ring opening of epoxides: a facile approach towards the synthesis of polyketides and related stereoenriched natural products: a review. Molecular Diversity.
DOI: 10.1007/s11030-024-11057-7

2023. Continuous Flow Generation of Highly Reactive Organometallic Intermediates: A Recent Update. Journal of Flow Chemistry.
DOI: 10.1007/s41981-023-00292-y

2022. Metal-mediated reactions of bromoform with electron-rich and electron-deficient carbon-carbon and carbon-hetero atom multiple bonds. Journal of Chemical Sciences.
DOI: 10.1007/s12039-022-02075-9