Product Name
1,1'-Bis(diphenylphosphino)ferrocene palladium(II)chloride dichloromethane complex, 97%
Molecular Formula
C35H30Cl2FeP2·PdCl2
Certificate of Analysis (COA)
Synonyms
Dichloro1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloromethane adduct
IUPAC Name
bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloromethane;dichloropalladium;iron(2+)
InChI Key
SNRCKKQHDUIRIY-UHFFFAOYSA-L
SMILES
CH-1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.CH-1C=CC(=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C(Cl)Cl.ClPdCl.Fe+2
🧑🔬 Catalyzing Cross-Coupling Reactions
This is its most central application. It is extensively used to catalyze a variety of cross-coupling reactions that form carbon-carbon and carbon-heteroatom bonds, making it an indispensable tool for constructing complex organic molecules.
Suzuki-Miyaura Coupling: Catalyzes the coupling of arylboronic acids with aryl halides, serving as one of the most important methods for synthesizing biaryl compounds, which are common structures in pharmaceuticals and materials.
Stille Coupling: Catalyzes the coupling of organotin compounds with halides.
Negishi Coupling: Catalyzes the coupling of organozinc compounds with halides.
Buchwald-Hartwig Amination: Catalyzes the coupling of aryl halides with amines, a key method for constructing arylamine compounds used in the synthesis of drugs and materials.
🧪 Other Catalytic Transformations
Beyond the coupling reactions mentioned above, Pd(dppf)Cl₂ is also an effective catalyst for various other transformations.
Borylation of Aryl Halides: Introduces boronate ester groups onto aromatic rings, providing precursors for further coupling reactions.
Carbonylation Reactions: Catalyzes reactions that introduce carbonyl groups.
Domino/Tandem Reactions: Used for the one-step construction of complex polycyclic molecules, such as in the synthesis of polyheterocycles.
⚛️ Synthetic Building Block and Ligand Precursor
The compound itself is a stable, well-defined organometallic complex. It can serve as a precursor to generate the actual catalytically active zero-valent palladium species (Pd(0)) in situ, or as a source of the bisphosphine ligand (dppf). Researchers also utilize its well-defined structure for spectroscopic studies to investigate catalytic reaction mechanisms
Q1: What is CAS 95464-05-4?
A: CAS 95464-05-4 is [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) Dichloromethane Adduct, commonly written as PdCl₂(dppf)·CH₂Cl₂.
Q2: What is PdCl₂(dppf)·CH₂Cl₂?
A: It is a palladium(II) complex containing the chelating dppf ligand and dichloride ligands, with one molecule of dichloromethane incorporated as a 1:1 adduct.
Q3: What is the molecular weight of CAS 95464-05-4?
A: The molecular weight is 816.64 g/mol.
Q4: What is the molecular formula?
A: The molecular formula is C₃₅H₃₀Cl₄FeP₂Pd, corresponding to the dppf-palladium dichloride complex with one molecule of dichloromethane.
Q5: What is PdCl₂(dppf)·CH₂Cl₂ used for?
A: It is mainly used as a palladium catalyst or catalyst precursor for cross-coupling reactions, particularly in synthetic organic and pharmaceutical chemistry.
Q6: Is it the same as PdCl₂(dppf)?
A: Not exactly. CAS 95464-05-4 is the dichloromethane adduct, written as PdCl₂(dppf)·CH₂Cl₂. The dichloromethane-free complex is a distinct material and should not be assigned the same CAS number.
Q7: What is dppf?
A: dppf stands for 1,1′-bis(diphenylphosphino)ferrocene, a bidentate phosphine ligand widely used in transition-metal catalysis.
Q8: How should CAS 95464-05-4 be stored?
A: Store the material tightly closed in a cool, dry environment and protect it from moisture and contamination. Product-specific storage recommendations should always be followed.