Copper (II) Methoxide
[CAS# 1184-54-9]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic copper
• Name: Copper (II) Methoxide
• Synonyms: Copper(2+) dimethanolate
• Molecular Formula: C₂H₆CuO₂
• Molecular Weight: 125.61
• CAS Registry Number: 1184-54-9
• EC Number: 627-155-2
• SMILES: CO[Cu]OC

Properties

• Melting point: 206 °C (decomp.)

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Risk Statements: H228-H302-H315-H319-H335
• Safety Statements: P210-P240-P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P370+P378-P403+P233-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

• Transport Information: UN 3181

Discovery and Applications

Copper(II) methoxide, a copper-based alkoxide, has gained significant attention in organic synthesis and materials science due to its unique reactivity and versatility. This compound, with the chemical formula Cu(OCH3)2, features copper in the +2 oxidation state coordinated to two methoxide (OCH3) groups. Its discovery and subsequent development were driven by the need for efficient copper-based reagents that could facilitate a range of chemical transformations, particularly in the field of organic synthesis.

The interest in copper(II) methoxide stems from the well-known catalytic properties of copper, particularly in oxidation reactions and C–O bond-forming processes. The methoxide ligands in copper(II) methoxide make it particularly reactive, allowing it to participate in various organic reactions, including oxidation and coupling reactions. One of the significant advantages of copper(II) methoxide is its ability to act as a mild and selective oxidizing agent, which has proven valuable in synthesizing complex organic molecules.

One of the primary applications of copper(II) methoxide is in the synthesis of aryl ethers and other oxygen-containing organic compounds. In these reactions, copper(II) methoxide can facilitate the coupling of aryl halides with alcohols, forming aryl ethers in good yields. This process, often referred to as the Ullmann-type etherification, is crucial in the synthesis of various pharmaceuticals, agrochemicals, and natural products. The ability of copper(II) methoxide to efficiently catalyze these reactions under relatively mild conditions has made it a valuable tool for organic chemists.

In addition to its role in etherification reactions, copper(II) methoxide has also been employed in the oxidative coupling of phenols, a reaction that leads to the formation of biaryl compounds. These biaryls are important structural motifs in many natural products and active pharmaceutical ingredients. The use of copper(II) methoxide in this context is particularly advantageous due to its selectivity and ability to operate under mild conditions, which helps preserve sensitive functional groups in the starting materials.

Beyond organic synthesis, copper(II) methoxide has applications in materials science, particularly in the preparation of copper-containing thin films and coatings. These films are used in various electronic and catalytic applications, where the copper serves as a conductive or catalytic material. The decomposition of copper(II) methoxide under controlled conditions allows for the deposition of high-purity copper films, which are essential in microelectronics and other advanced technologies.

In summary, copper(II) methoxide is a versatile reagent with applications ranging from organic synthesis to materials science. Its ability to act as a catalyst in oxidation and coupling reactions, as well as its role in the preparation of copper-containing films, underscores its importance in both academic research and industrial applications.

References

2021. Magnetic properties of methanolate copper(II) coordination polymer-containing dicyanamide and 4,4′-bipyridine. Magnetic Properties of Paramagnetic Compounds, Magnetic Susceptibility Data, Volume 4.
DOI: 10.1007/978-3-662-62474-6_338

2019. Synthesis of 4H-Pyrimido[2,1-b]benzothiazoles with a Heterogeneous Cu(II) Catalyst. Synfacts.
DOI: 10.1055/s-0037-1612390

1990. Superconducting oxide YBa2Cu3O7−x prepared by the metal alkoxide method. Journal of Materials Research.
DOI: 10.1557/jmr.1990.0683