84680-95-5

Basic information

• Product Name: 1,1'-BIS(DI-TERT-BUTYLPHOSPHINO)FERROCENE
• Synonyms: 1,1'-BIS(DI-T-BUTYLPHOSPHINO)FERROCENE;1,1'-BIS(DI-TERT-BUTYLPHOSPHINO)FERROCENE;BIS[(DI-TERT-BUTYLPHOSPHINO)CYCLOPENTADIENYL]IRON;1,1'-Bis(di-t-butylphosphino)ferrocene,min.98%;1,1'-Bis(di-tert-butylphosphino)ferrocene,min. 98%;1,1'-Bis(di-t-butylphosphino)ferrocene, min. 98%;1,1'-Bis(di-tert-butylphosphino)ferrocene ,98%;98% DtBPF
• CAS NO: 84680-95-5
• Molecular Formula: C₂₆H₄₄FeP₂
• Molecular Weight: 474.42
• EINECS: 1533716-785-6
• Product Categories: Classes of Metal Compounds;Fe (Iron) Compounds;Ferrocenes;Metallocenes;Phosphine Ligands;Synthetic Organic Chemistry;Transition Metal Compounds;Catalysis and Inorganic Chemistry;Phosphorus Compounds;Polydentate Phosphine Ligands;Achiral Phosphine;Aryl Phosphine
• Mol File: 84680-95-5.mol

Chemical Properties

• Melting Point: 181-182°C (dec.)
• Appearance: orange to red/crystal
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: 1,1'-BIS(DI-TERT-BUTYLPHOSPHINO)FERROCENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-BIS(DI-TERT-BUTYLPHOSPHINO)FERROCENE(84680-95-5)
• EPA Substance Registry System: 1,1'-BIS(DI-TERT-BUTYLPHOSPHINO)FERROCENE(84680-95-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37/39-26
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 84680-95-5(Hazardous Substances Data)

Usage

Uses

Used in Organometallic Chemistry:
1,1'-Bis(di-tert-butylphosphino)ferrocene is used as an organometallic ligand for its ability to form stable complexes with various metal centers. Its steric and electronic properties contribute to the stability and reactivity of the resulting complexes.
Used in Palladium-Catalyzed Amination:
In the field of palladium-catalyzed amination reactions, 1,1'-bis(di-tert-butylphosphino)ferrocene is used as a sterically hindered chelating alkyl phosphine ligand. Its presence accelerates the rate of amination of unactivated aryl chlorides, enhancing the efficiency and selectivity of the reaction.
Used in Catalyst Design:
1,1'-Bis(di-tert-butylphosphino)ferrocene is employed in the design of catalysts for various organic transformations, such as cross-coupling reactions, due to its ability to modulate the electronic and steric properties of the active metal center. This allows for fine-tuning of the catalyst's performance and selectivity in specific applications.

Reaction

Ligand for synthesis of polycyclic indoles via Pd-catalyzed intramolecular heteroannulation. Ligand for the palladium-catalyzed intramolecular arylation of aryl bromides under mild conditions. Ligand for cross-coupling reactions between bromoarenes and potassium allyltrifluoroborates promoted by a catalyst prepared from Pd(OAc)2 and DTBPF selectively providing γ-coupling products. Ligand for the copper-catalyzed system for the ?-boration of of a variety of α,?-unsaturated amides. Ligand for the synthesis of Paucifloral F and related indanone analogues via palladium-catalyzed α-arylation. Ligand for the Pd-carbon monoxide complex catalyzed hydroxycarbonylation of aryl halides. Ligand for the palladium-catalyzed β-C-glycosylation by decarboxylative allylation to normal pyran systems,and cis-2,6-disubstituted tetrahydropyrans. Pd-catalyzed dearomative indole bisfunctionalization via a diastereoselective arylcyanation. Ligand for the copper- DTBPF catalyzed C–H activation and carboxylation of terminal alkynes.

Upstream product

• 65587-59-9 1,1'-dilithioferrocene-(N,N,N',N'-tetramethylethylenediamine)-(1/2) 
• 13716-10-4 di(tert-butyl)chlorophosphine 

Downstream Products

• 565441-22-7 (1,1'-bis(di-tert-butylphosphino)ferrocene)Pd(Br)(C₆H₄-4-CN) 
• 221676-01-3 Pd(1,1'-bis(di-tert-butylphosphino)ferrocene)(Br)(C₆H₅) 
• 565441-47-6 (CO)3Ni(1,1'-bis(di-tert-butylphosphino)ferrocene)Ni(CO)3 
• 1144038-59-4 [(η5-C5H4PtBu2)Fe(η5-C5H4PtBu2(C6F4)BF(C6F5)2)] 

Relevant articles and documents

A ferrocene diphosphine ligand preparation method

The invention discloses a method for preparing ferrocene diphosphine ligand, and belongs to the field of organic synthesis. The method comprises the following steps: by taking ferrocene as an initial raw material and boron trifluoride diethyl etherate as a catalyst, reacting with diaryl phosphine oxide or dialkyl phosphine oxide, hydrolyzing so as to obtain tertfluoborate of a ferrocene diphosphine compound, and performing heating backflow deprotection in methanol, thereby obtaining the ferrocene diphosphine compound. Compared with the prior art, the method is gentle in reaction condition, simple in aftertreatment, and relatively applicable to industrial production, and the yield is greater than 90%. The prepared ferrocene diphosphine can be used as ligand of a metal catalyst, and can be used in the fields such as organic optoelectronic materials and medicines.

Structure of the hydrogenation catalyst [(P P)Rh(NBD)]ClO4, P P = (η5-[(CH3)3C]2PC 5H4)2Fe, and some comparative rate studies

The structure of the hydrogenation catalyst precursor [(P P)Rh(NBD)]ClO4 [P P = (η5-[(CH3)3C]2PC 5H4)2Fe; NBD = norbornadiene] has been determined. The cationic moiety finds Rh in a very distorted square-planar environment coordinated to the double bonds of the norbornadiene ligand at distances of 2.181 (5) and 2.161 (5) A? and the phosphorus atoms of the bidentate chelating phosphine ligand at distances of 2.466 (1) and 2.458 (1) A?. Relative rate studies, employing the aforementioned catalyst precursor and also the related precursor where P P = (η5-[(C6H5)2PC5H 4]2Fe), have been performed for the hydrogenation reactions of (acylamino)acrylic, (acylamino)cinnamic, itaconic, and methylcinnamic acids in methanol and/or ethanol. The results of these experiments, together with related work previously reported, are discussed and rationalized in terms of the steric and electronic effects exerted by the substituents attached to the chelating bis(phosphine) ligands.