95464-05-4

Basic information

• Product Name: 1,1'-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex
• Synonyms: DICHLORO[1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE]-PALLADIUM DICHLOROMETHANE ADDUCT;DICHLORO[1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE]PALLADIUM(II) DICHLOROMETHANE ADDUCT;DICHLORO[1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE]PALLADIUM(II) DICHLOROMETHANE COMPLEX;1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENEPALLADIUM(II) DICHLORIDE, DICHLOROMETHANE;1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE-PALLADIUM(II)DICHLORIDE DICHLOROMETHANE COMPLEX;[1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE]DICHLOROPALLADIUM(II), COMPLEX WITH DICHLOROMETHANE (1:1);[1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE]DICHLOROPALLADIUM(II), DCM ADDUCT;[1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE]DICHLOROPALLADIUM(II), DICHLOROMETHANE ADDUCT
• CAS NO: 95464-05-4
• Molecular Formula: C₃₄H₂₈Cl₂FeP₂Pd
• Molecular Weight: 816.64
• EINECS: 460-040-3
• Product Categories: Catalysis and Inorganic Chemistry;Homogeneous Pd Catalysts;Palladium;Pd
• Mol File: 95464-05-4.mol
• Article Data: 21

Chemical Properties

• Melting Point: 275-280 °C(lit.)
• Appearance: orange-red/Powder
• Density: 1 g/cm3
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility: Insoluble in water.
• Stability: Light Sensitive
• CAS DataBase Reference: 1,1'-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex(95464-05-4)
• EPA Substance Registry System: 1,1'-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex(95464-05-4)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-40-67-48/20/22
• Safety Statements: 23-24/25-26-36/37
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 95464-05-4(Hazardous Substances Data)

Usage

Reaction

Catalyst for the borylation of aryl halides. β-Alkyl Suzuki-Miyaura cross-coupling reactions with potassium alkyltrifluoroborates. Catalyst for modified Negishi coupling. Synthesis of polyheterocycles by a Pd-catalyzed intramolecular N-arylation/C-H bond activation/aryl-aryl bond-forming domino process. Catalyst for Stille allylation. Catalyst for the amination of aryl bromides.

Chemical Properties

orange/red solid

Uses

Different sources of media describe the Uses of 95464-05-4 differently. You can refer to the following data:
1. suzuki reaction
2. 1,1'-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex is used in the preparation of imidazoles, benzimidazoles, and tetrahydropyrimidines,it is also used as a catalyst for Suzuki and Stile couplings.
3. Used as a catalyst for Suzuki and Stile couplings.

Upstream product

• 12150-46-8 1,1'-bis-(diphenylphosphino)ferrocene 
• 14323-43-4 diamminedichloropalladium(II) 
• 124268-93-5 {1,1'-bis(diphenylphosphino)ferrocene} palladium dibromide 
• 75-09-2 dichloromethane 
• 532-31-0 silver benzoate 
• 12317-46-3 dichloro(norbornadiene)palladium(II) 
• 21264-30-2 dichloro bis(acetonitrile) palladium(II) 
• 12107-56-1 dichloro(cycloocta-1,5-diene)palladium (II) 
• 15617-18-2 bis(benzonitrile)palladium(II) dichloride 
• 532-32-1 sodium benzoate 
• 112220-68-5 bis(μ-chloro)bis(1,1'-bis(diphenylphosphino)ferrocene)dipalladium(II) tetrafluoroborate 
• 75-05-8 acetonitrile 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 590420-33-0 Pd(η2-CH2=CHCHO)(dppf) 

Downstream Products

• 262433-07-8 N₁-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-phenylbenzene]-1-benzenesulfonamide 
• 262433-09-0 1-(phenylsulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline 
• 262433-12-5 N₁-[2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N₁-methyl-1-benzenesulfonamide 
• 474111-79-0 methyl 3-[(2R)-2-({(tert-butoxycarbonyl)[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-pyridinyl)ethyl]amino}methyl)-3,4-dihydro-2H-chromen-6-yl]benzoate 
• 477252-06-5 N-Isopropyl-1-[3-(3-acetyl-4-hydroxyphenyl)phenyl]-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide 
• 129013-83-8 3-(4-bromophenyl)pyridine 
• 305800-55-9 3-(4,4-dimethyl-8-methoxy-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-5-fluorobenzonitrile 
• 317826-94-1 2-[1-(3-Nitrophenyl)ethylamino]-4-[benzimidazol-1-yl]-6-(furan-3-yl)pyrimidine 
• 317826-93-0 2-[1-(3-Nitrophenyl)ethylamino]-4-[benzimidazol-1-yl]-6-(2-methylphenyl)pyrimidine 
• 123102-32-9 methyl 2-amino-6-ethyl benzoate 
• 112220-70-9 bis(μ-hydroxy)bis(1,1'-bis(diphenylphosphino)ferrocene)dipalladium(II) tetrafluoroborate 
• 403609-44-9 [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) 3,6-dichloro-1,2-benzenedithiolate 

Relevant articles and documents

The thiosulfate (S2O32?) ion; a neglected but simple hetero-donor ligand towards platinum(II), palladium(II) and nickel(II)

Reactions of the thiosulfate ligand (as sodium thiosulfate, Na2S2O3·5H2O) with phosphine complexes of the group 10 metals Ni(II), Pd(II) and Pt(II) resulted in five neutral thiosulfate complexes, [Ni(S2O3)(dppe)] (dppe = Ph2PCH2CH2PPh2), [Pd(S2O3)(dppe)], [Pd(S2O3)(dppf)] (dppf = Fe(C5H4PPh2)2), [Pd(S2O3)(PPh3)2] and [Pt(S2O3)(PPh3)2]. X-ray structure determinations of [Pd(S2O3)(dppf)], [Pd(S2O3)(PPh3)2] and [Pt(S2O3)(PPh3)2] confirmed that thiosulfate ligand coordinates as a bidentate chelating ligand via both sulfur and oxygen donor atoms. In addition, reactions of the thiosulfate ligand with dinuclear chloride-bridged cyclopalladated complexes gave four mononuclear anionic complexes [Pd(S2O3)(damp)]? (damp = N,N-dimethylbenzylamino, (CH3)2NCH2C6H4), [Pd(S2O3)(ptpy)]? (ptpy = p-tolylpyridyl), ]Pd(S2O3)(bzpy)]? (bzpy = 2-benzylpyridyl) and [Pd(S2O3))pap)]? (pap = 2-(phenylazo)phenyl). The structure of (Ph3PCH2Ph)[Pd(S2O3)(pap)] by X-ray crystallography revealed the ability of thiosulfate ligand to cleave the bridging chloride ligand on the starting complexes by acting as an S,O-donor chelating ligand. An ESI mass spectrometric investigation showed that the coordinated thiosulfate ligand undergoes fragmentation at elevated capillary exit voltages.

Preparation method of [1, 1'-bis (diphenylphosphino) ferrocene] palladium dichloride

The invention discloses a preparation method of [1, 1'-bis (diphenylphosphino) ferrocene] palladium dichloride, which comprises the following steps of: (a) adding palladium powder into an aqua regia solution, heating for dissolution, adding hydrochloric acid while the solution is hot to drive nitrate, cooling, and adding an ethanol-water mixed solution for dilution; (b) dissolving 1, 1'-bis (diphenylphosphino) ferrocene (dppf) in an organic solvent in a stirring state to obtain an organic solution of 1, 1'-bis (diphenylphosphino) ferrocene; and (c) dropwise adding the solution obtained in thestep (a) into the solution obtained in the step (b), stirring for reaction, cooling, filtering, washing, draining, and carrying out vacuum drying to obtain a red [1, 1'-bis (diphenylphosphino) ferrocene] palladium dichloride complex crystal. The initial raw material palladium powder is directly used for replacing palladium dichloride, the target product is directly synthesized, the synthesis period is shortened, the reaction steps are simplified, the efficiency is improved, the production cost is reduced, the yield of the target product is larger than 99%, and the purity of the target productis larger than 99%.

Reactivity of hemilabile pyridyl- and methyl-substituted pyrimidylselenolates with [MCl2(dppf)] (M?=?Pd, pt; dppf?=?bis(diphenylphisphino)ferrocene)

The bis(diphenylphisphino)ferrocene (dppf) derived palladium analogue of [PdCl2(dppf)] on reaction with the sodium salt of pyridyl/pyrimidyl selenolate yielded mononuclear cis configured complex [Pd(SeAr)2(dppf)] (Ar = C5H