Bis(dipivaloylmethanato)copper
[CAS# 14040-05-2]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic copper
• Name: Bis(dipivaloylmethanato)copper
• Synonyms: Bis(2,2,6,6-tetramethyl-3,5-heptanedionato)copper; Bis(dipivaloylmethanato)copper(II); Bis(2,2,6,6-tetramethyl-3,5-heptanedione)copper; Bis(hexamethylacetylacetonato)copper(II); Copper bis(2,2,6,6-tetramethyl-3,5-heptanedionate); Copper bis(2,2,6,6-tetramethyl-3,5-heptanedione); Cupric 2,2,6,6-tetramethyl-3,5-heptanedionate; Di(dipivaloylmethanato)copper
• Molecular Formula: C₂₂H₃₈CuO₄
• Molecular Weight: 430.09
• CAS Registry Number: 14040-05-2
• EC Number: 626-948-0
• SMILES: CC(/C(=C/C(=O)C(C)(C)C)/[O-])(C)C.CC(/C(=C/C(=O)C(C)(C)C)/[O-])(C)C.[Cu+2]

Properties

• Melting point: 196-198 °C
• Boiling point: 315 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

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

Discovery and Applications

Bis(dipivaloylmethanato)copper, commonly known as copper(II) bis(dipivaloylmethanato), is a versatile organometallic compound with significant implications in materials science and catalysis. Its unique structure, featuring copper coordinated with two dipivaloylmethanato ligands, endows it with distinct chemical and physical properties that are leveraged in various applications.

The discovery of Bis(dipivaloylmethanato)copper dates back to efforts to design copper complexes with improved stability and catalytic efficiency. The dipivaloylmethanato ligand, characterized by its bulky tert-butyl groups, stabilizes the copper center by creating a chelating effect. This ligand imparts enhanced stability to the metal center, making the complex suitable for various chemical processes.

One of the primary applications of Bis(dipivaloylmethanato)copper is in the field of catalysis. The compound is utilized as a catalyst in several organic transformations due to its ability to activate substrates and facilitate reactions. In particular, it has been employed in the catalysis of oxidative coupling reactions, where it helps in the formation of C-C bonds. The stability imparted by the dipivaloylmethanato ligands allows for the efficient catalysis of these reactions under mild conditions.

Additionally, Bis(dipivaloylmethanato)copper is used in the synthesis of advanced materials. Its coordination properties make it a valuable precursor in the formation of copper-containing polymers and materials. The compound can be incorporated into polymer matrices to create materials with specific electronic and optical properties. For example, it has been used to develop organic-inorganic hybrid materials with applications in electronics and photonics.

The complex is also explored for its potential in electronic applications. The copper center, combined with the bulky dipivaloylmethanato ligands, can influence the electronic properties of the material, making it suitable for use in organic semiconductors and light-emitting devices. The tunability of these properties is valuable for designing devices with specific performance characteristics.

In addition to its role in catalysis and materials science, Bis(dipivaloylmethanato)copper is studied for its potential in other areas, such as bioinorganic chemistry and environmental applications. Its stability and reactivity make it a candidate for further research in these fields, where it could contribute to the development of new technologies and materials.

In summary, Bis(dipivaloylmethanato)copper is a significant compound in organometallic chemistry with diverse applications in catalysis, materials science, and electronics. Its unique structure and properties make it a valuable tool for researchers seeking to develop advanced materials and catalytic systems.

References

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