Allyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloropalladium(II)
[CAS# 478980-03-9]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic palladium
• Name: Allyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloropalladium(II)
• Synonyms: CX21
• Molecular Formula: C₃₀H₄₁ClN₂Pd
• Molecular Weight: 571.53
• CAS Registry Number: 478980-03-9
• EC Number: 625-870-4
• SMILES: CC(C)c1cccc(c1n2ccn(c2=[Pd](CC=C)Cl)c3c(cccc3C(C)C)C(C)C)C(C)C

Properties

• Melting point: >300 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

Allyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloropalladium(II) is a significant compound in the field of organometallic chemistry, known for its application as a catalyst in various chemical reactions. This substance, often abbreviated as a Pd(II) complex with a specific N-heterocyclic carbene (NHC) ligand, showcases unique properties that make it valuable in synthetic chemistry.

The discovery of Allyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloropalladium(II) stems from ongoing research aimed at developing more efficient and versatile catalysts for organic transformations. The synthesis of this compound involves the coordination of an NHC ligand with a palladium center. The NHC ligand, specifically 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, is known for its strong electron-donating properties and stability, which enhance the reactivity and selectivity of the palladium catalyst.

To prepare Allyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloropalladium(II), the NHC ligand is reacted with a palladium(II) chloride precursor, followed by the addition of an allyl group. This process typically requires precise control of reaction conditions to achieve high yields and purity. The resulting complex is characterized by its structure, which includes a palladium center coordinated to both the NHC ligand and an allyl group, with a chloride ion completing the coordination sphere.

In terms of applications, Allyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloropalladium(II) is primarily used as a catalyst in cross-coupling reactions, such as the Suzuki-Miyaura and Heck reactions. The presence of the NHC ligand enhances the stability and reactivity of the palladium center, allowing for efficient coupling of various organic substrates. This catalyst is particularly valued for its ability to facilitate reactions with high selectivity and under mild conditions, which is crucial for synthesizing complex organic molecules and pharmaceuticals.

Additionally, the compound has applications in polymer chemistry, where it is employed in the polymerization of olefins and other monomers. The catalytic properties of Allyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloropalladium(II) enable the controlled formation of polymers with specific properties, such as molecular weight and structure. This application is important for the development of advanced materials with tailored characteristics for various industrial uses.

The handling and storage of Allyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloropalladium(II) require precautions due to its chemical reactivity. It should be stored in a dry, cool place, protected from air and moisture, to maintain its stability and effectiveness as a catalyst.

Future research on this compound may focus on expanding its applications and optimizing its performance in various catalytic processes. Investigations into its interactions with different substrates and reaction conditions could lead to new advancements in synthetic chemistry and materials science.