Bis(2-diphenylphosphanylcyclopenta-2,4-dien-1-yl)iron

Base Information

• Chemical Name: Bis(2-diphenylphosphanylcyclopenta-2,4-dien-1-yl)iron
• CAS No.: 12150-46-8
• Molecular Formula: C34H28FeP2
• Molecular Weight: 556.407
• Hs Code.: HOSPHINO)FERROCENE PRODUCT IDENTIFICATION
• Mol file: 12150-46-8.mol

Synonyms:SCHEMBL15415366;bis(2-diphenylphosphanylcyclopenta-2,4-dien-1-yl)iron;Bis[3-(diphenylphosphanyl)cyclopenta-2,4-dien-1-yl]iron

Chemical Property of Bis(2-diphenylphosphanylcyclopenta-2,4-dien-1-yl)iron

Chemical Property:

• Appearance/Colour: deep yellow crystalline powder
• Melting Point: 181-182 °C (dec.)(lit.)
• Boiling Point: 363.8oC at 760mmHg
• Flash Point: 182.8oC
• PSA: 27.18000
• LogP: 6.38890
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: Soluble in chloroform, dichloromethane, alcohol and pentane. Insoluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 554.101560
• Heavy Atom Count: 37
• Complexity: 499

Purity/Quality:

98% ^*data from raw suppliers

1,1’-Bis(diphenylphosphino)ferrocene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xn,Xi
• Hazard Codes: T,Xi,Xn
• Statements: 25-36/37/38-20/21/22
• Safety Statements: 22-24/25-45-28A-36-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical 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.[Fe+2]
• General Description: 1,1'-Bis(diphenylphosphino)ferrocene (DPPF) is a versatile bidentate phosphine ligand widely used in coordination chemistry and catalysis. It stabilizes metal complexes, such as palladium catalysts in cyanation reactions and copper(I) chalcogenide clusters, by acting as a chelating agent. Its redox-active ferrocene backbone and strong coordination ability enhance reaction efficiency, enabling high yields and functional group tolerance in synthetic applications. Additionally, DPPF's role in stabilizing metal centers and modulating reaction kinetics highlights its importance in organometallic chemistry and materials science.

Technology Process of Bis(2-diphenylphosphanylcyclopenta-2,4-dien-1-yl)iron

There total 14 articles about Bis(2-diphenylphosphanylcyclopenta-2,4-dien-1-yl)iron which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

[Fe(η5-C5H4P(OPh)2)2] (405164-68-3) → 1,1'-bis-(diphenylphosphino)ferrocene (12150-46-8)

Guidance literature:

With tributylphosphine; iodine; In tetrahydrofuran; acetonitrile; at 20 ℃; for 0.166667h; Inert atmosphere;

Reference yield: 92.0%

1,1'-bis(diphenylphosphino)ferrocene tetrafluoroborate → 1,1'-bis-(diphenylphosphino)ferrocene (12150-46-8)

Guidance literature:

In methanol; for 8h; Reflux;

Reference yield: 84.0%

lithium diphenylphosphinocyclopentadienyl (83272-80-4) + iron(II) chloride + 1,2-bis(diphenylphosphanyl)-4-tert-butylcyclopentadienyl lithium → 1,1'-bis-(diphenylphosphino)ferrocene (12150-46-8) + 1,1′,2,2′-tetrakis(diphenylphosphino)-4,4′-di-tert-butylferrocene (403815-19-0) + 1,1',2'-tris(diphenylphosphino)-4-tert-butylferrocene (878190-65-9)

Guidance literature:

In tetrahydrofuran; (Ar); dropwise addn. of a soln. of trisubstituted lithium compd. in THF to a suspn. of iron salt in THF at -40°C, stirring for 2 h at room temp., addn. of a soln. of monosubstituted lithium salt in THF at -40°C; evapn., reflux in toluene for 3 h, cooling, filtration, column chromy. (SiO2, toluene/hexane 4:1); elem. anal.;

DOI:10.1021/om050882g

upstream raw materials:

1,1'-dilithioferrocene

phenylthiodiphenylphosphine

phenyllithium

chloro-diphenylphosphine

Downstream raw materials:

2-cyano-5-methyl-benzoic acid methyl ester

ethyl [[4-[2-(5-cyano-2-methoxybenzenesulfonylamino)-ethyl]-2'-methanesulfonylbiphenyl-3-yl]amino]acetate

2-(4-cyano-2-nitrophenylmethyl)benzoic Acid Methyl Ester

1-[3-(methylsulfanylmethyl)phenyl]-pyrrolidine

Refernces

Synthesis of phthalonitriles using a palladium catalyst

10.1055/s-2008-1078269

The research presents an innovative and efficient method for synthesizing phthalonitriles from o-dibromobenzenes under mild conditions. The purpose of this study is to develop an alternative to the traditional Rosenmund–von Braun reaction, which often suffers from low yields and harsh reaction conditions. The researchers utilized key chemicals such as Zn(CN)?, tris(dibenzylideneacetone)dipalladium (Pd?(dba)?), and 1,1′-bis(diphenylphosphino)ferrocene (DPPF) as catalysts in dimethylacetamide (DMAC) solvent. The method demonstrated high yields (between 62% and 97%) and was effective for various o-dibromobenzenes with different substituents, including electron-donating and electron-withdrawing groups. The study concluded that this palladium-catalyzed cyanation method is a significant improvement over existing methods, offering milder conditions, higher yields, and the ability to tolerate a wide range of functional groups without the formation of unwanted byproducts.

Copper chalcogenide clusters stabilized with ferrocene-based diphosphine ligands

10.1021/ic3021854

The study focuses on the synthesis and characterization of copper(I) chalcogenide clusters stabilized by the redox-active diphosphine ligand 1,1′-bis(diphenylphosphino)ferrocene (dppf). The researchers used copper(I) acetate coordination complex (dppf)CuOAc (5) and reacted it with 0.5 equivalents of E(SiMe3)2 (where E = S, Se, Te) to prepare the clusters [Cu12(μ4-S)6(μ-dppf)4] (1), [Cu8(μ4-Se)4(μ-dppf)3] (2), [Cu4(μ4-Te)(μ4-η2-Te2)(μ-dppf)2] (3), and [Cu12(μ5-Te)4(μ8-η2-Te2)2(μ-dppf)4] (4). These chalcogenide clusters serve to explore the utility of the bidentate phosphine-based ferrocene ligand for the surface passivation of copper chalcogen frameworks, with the dppf ligands playing a crucial role in stabilizing the {Cu2xEx} cores and protecting the clusters from decomposition or further condensation into bulk solids. The study aimed to understand the redox properties and coordination abilities of these clusters, which could have implications for the development of functional materials.

Kinetics of complex formation between palladium(II) acetate and bis(diphenylphosphino)ferrocene

10.1016/j.poly.2008.11.038

The study investigates the kinetics of complex formation between palladium(II) acetate and 1,1’-bis(diphenylphosphino)ferrocene (dppf) in CDCl3 and DMSO-d6 solvents using 31P NMR spectroscopy. Palladium(II) acetate acts as the metal source, while dppf serves as the ligand. In CDCl3, the reaction directly forms the [Pd(dppf)(OAc)2] species with dppf acting as a chelate ligand. In DMSO-d6, an intermediate is initially formed, which then converts into the more stable [Pd(dppf)(OAc)2] species. The rate constants for these reactions were determined through computer fitting of integration-time data, revealing that complex formation is faster in CDCl3 than in DMSO-d6, likely due to DMSO's coordinating ability, which slows the coordination of dppf and decreases the electrophilicity of the metal center.