Chloro[2-(di-tert-butylphosphino)-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl)]palladium(II)
[CAS# 1142811-12-8]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Biphenyl compounds
• Name: Chloro[2-(di-tert-butylphosphino)-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl)]palladium(II)
• Synonyms: tBuXPhos Pd G1
• Molecular Formula: C₃₇H₅₅ClNPPd
• Molecular Weight: 686.70
• CAS Registry Number: 1142811-12-8
• EC Number: 689-565-8
• SMILES: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C(C)(C)C)C(C)(C)C)C(C)C.C1=CC=C([C-]=C1)CCN.Cl[Pd+]

Properties

• Melting point: 150-159 ºC (Expl.)

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Hazard Statements: H315-H319-H335-H351
• Precautionary Statements: P202-P261-P264-P302+P352-P305+P351+P338-P308+P313

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Carcinogenicity	Carc.	2	H351

Discovory and Applicatios

Chloro[2-(di-tert-butylphosphino)-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl)]palladium(II), often referred to as a palladium complex with phosphine and amine ligands, is a well-established compound in the field of organometallic chemistry. This type of complex is part of the broader family of palladium-based catalysts, which are commonly used in various types of chemical reactions, particularly in the area of organic synthesis and catalysis.

The discovery of palladium-based catalysts, including those involving phosphines and amines, dates back to the early 20th century. However, the specific compound Chloro[2-(di-tert-butylphosphino)-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl)]palladium(II) is typically utilized in more specialized applications that require precise control over the reactivity of the palladium center. The use of both phosphine and amine ligands in the coordination sphere of palladium is significant, as it allows for fine-tuning the electronic properties of the metal, making it suitable for a variety of catalytic processes.

This compound is often employed in cross-coupling reactions, such as the Suzuki-Miyaura reaction, which is a cornerstone of modern organic synthesis. Cross-coupling reactions involve the formation of carbon-carbon bonds between two organic molecules, typically using a palladium catalyst. The specific ligands present in Chloro[2-(di-tert-butylphosphino)-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl)]palladium(II) are chosen to provide optimal stability to the palladium center while enhancing its catalytic activity.

Another application of this type of palladium complex is in the development of new materials, such as polymers and pharmaceuticals. The ability of palladium complexes to mediate a variety of bond-forming reactions is essential in the synthesis of complex molecular architectures, which are critical in the creation of new functional materials. The amine and phosphine ligands can be specifically chosen for their ability to stabilize the palladium metal, which in turn allows for more efficient catalysis in the creation of these materials.

The compound also finds use in the field of medicinal chemistry, where palladium-based catalysts are employed to facilitate the construction of bioactive molecules. The versatility of palladium catalysts, including those like Chloro[2-(di-tert-butylphosphino)-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl)]palladium(II), makes them ideal for complex drug synthesis, particularly in the formation of heterocyclic structures, which are common in many pharmaceutical agents.

In conclusion, Chloro[2-(di-tert-butylphosphino)-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl)]palladium(II) is an important compound in the realm of organometallic chemistry, with applications in synthetic chemistry, material science, and drug development. Its ability to catalyze a variety of reactions, particularly those requiring the formation of carbon-carbon bonds, has made it a crucial tool in modern organic and medicinal chemistry.

References

1142811-12-8|Chloro[2-(di-tert-butylphosphino)-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl)]palladium(II)|2023. TXPhos: a highly stable and efficient ligand designed for ppm level Pd-catalyzed Suzuki-Miyaura coupling in water. Green Chemistry, 25(17).
DOI: 10.1039/D2GC04885J

2014. t-BuXPhos: a highly efficient ligand for Buchwald-Hartwig coupling in water. Green Chemistry, 16(9).
DOI: 10.1039/C4GC00853G

2013. Design and preparation of new palladium precatalysts for C-C and C-N cross-coupling reactions. Chemical Science, 4(2).
DOI: 10.1039/C2SC20903A