15629-92-2

Basic information

• Product Name: [1,3-Bis(diphenylphosphino)propane]nickel(II) chloride
• Synonyms: 1.3-Bis(dipheny phosphine) propane nickel(II)chloride;DICHLORO[1,3-BIS-(DIPHENYLPHOSPHINO)PROPANE] NICKE;NICL2(DPPP)/ 1,3-BIS(DIPHENY PHOSPHINE) PROPANE NICKEL(II)CHLORIDE;NiCl2(DPPP)NiCl2(DPPP);1,3-Bis-(diphenylphosphino)-propane nickel chloride;1,3-Bis(diphenyl phosphine)propane nickel(II)dichloride;Dichlorobis(1,3-diphenylphosphino)propaneünickel(II), C 59.9%;(1,3-dppp)NiCl2, 1,3-Bis(diphenylphosphino)propane nickel(II) chloride
• CAS NO: 15629-92-2
• Molecular Formula: C₂₇H₂₆P₂*Cl₂Ni
• Molecular Weight: 542.04
• EINECS: 1312995-182-4
• Product Categories: Metal Compounds;Boron, Nitrile, Thio,& TM-Cpds;Catalysts for Organic Synthesis;Classes of Metal Compounds;Homogeneous Catalysts;Metal Complexes;Ni (Nickel) Compounds;Synthetic Organic Chemistry;Transition Metal Compounds;metal-phosphine complexes;Ni
• Mol File: 15629-92-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 213 °C (dec.)(lit.)
• Boiling Point: 529.7 °C at 760 mmHg
• Flash Point: 291.5 °C
• Appearance: red/crystal
• Vapor Pressure: 9E-11mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: insoluble
• CAS DataBase Reference: [1,3-Bis(diphenylphosphino)propane]nickel(II) chloride(CAS DataBase Reference)
• NIST Chemistry Reference: [1,3-Bis(diphenylphosphino)propane]nickel(II) chloride(15629-92-2)
• EPA Substance Registry System: [1,3-Bis(diphenylphosphino)propane]nickel(II) chloride(15629-92-2)

Safety Data

• Hazard Codes: T,Xn
• Statements: 49-36/37/38-42/43-40
• Safety Statements: 53-26-36/37/39-45-24-22
• RIDADR: 3282
• WGK Germany: 3
• F: 10-21
• TSCA: No
• Hazardous Substances Data: 15629-92-2(Hazardous Substances Data)

Usage

Reaction

Nickel catalyst used in the N-heterocycle-directed cross-coupling of fluorinated arenes with organozinc reagents. Nickel catalyst used in the (E)-selective semihydrogenation of internal alkynes. Nickel catalyst used in the borylation of halides and pseudohalides.

Chemical Properties

red to red-brown powder or crystals

Uses

Different sources of media describe the Uses of 15629-92-2 differently. You can refer to the following data:
1. suzuki reaction.Dichloro[bis(1,3-diphenylphosphino)propane]nickel(II) is used as an effective catalyst for Kumada coupling and Suzuki reactions. It also catalyzes other reactions to convert enol ethers, dithioacetals and vinyl sulfides to olefins. Further, it is used as a catalyst for preparation of block-copolythiophenes and solid state metathesis polycondensation.
2. Dichloro[bis(1,3-diphenylphosphino)propane]nickel(II) is used as an effective catalyst for Kumada coupling and Suzuki reactions. It also catalyzes other reactions to convert enol ethers, dithioacetals and vinyl sulfides to olefins. Further, it is used as a catalyst for preparation of block-copolythiophenes and solid state metathesis polycondensation.

Application

Catalyst for:Synthesis of block-copolythiophenesSuzuki-Miyaura cross-coupling reaction of aryl halides with arylboronic acidsSolid state metathesis polycondensationPolymerization of poly(3-alkoxythiophene)sDiastereoselective Nozaki-Hiyama-Kishi coupling reactions of C1-C19 fragment of macrolide antibiotic aplyronine ATransfer condensation polymerization of conjugated polymers[1,3-Bis(diphenylphosphino)propane]dichloronickel(II) can be used as a precursor to synthesize metal-fullerene coordination complexes by reduction method.

InChI:InChI=1/C27H26P2.2ClH.Ni/c1-5-14-24(15-6-1)28(25-16-7-2-8-17-25)22-13-23-29(26-18-9-3-10-19-26)27-20-11-4-12-21-27;;;/h1-12,14-21H,13,22-23H2;2*1H;/q;;;+2/p-2

Upstream product

• 6737-42-4 1,3-bis-(diphenylphosphino)propane 
• 83864-14-6 nickel dichloride 

Downstream Products

• 83495-30-1 5,5′-diphenyl-2,2′-bithiophene 
• 492-97-7 2,2'-Bithiophene 
• 63877-96-3 2-(4-fluorophenylmethyl)thiophene 
• 189328-91-4 2-methyl-3-(4-fluorophenylmethyl)thiophene 
• 614730-10-8 methyl 3-methoxy-6-methylpyrazine-2-carboxylate 
• 15629-49-9 bis(1,3-bis(diphenylphosphino)propane)nickel⁽⁰⁾ 
• 32475-60-8 (dppp)Ni(CO)₂ 
• 90526-43-5 (Ni((C₆H₅)2PCH₂CH₂CH₂P(C₆H₅)2)Cl₃) 
• 82865-15-4 [Ni(Se₂C₂(CO₂CH₃)2)((C₆H₅)2PC₃H₆P(C₆H₅)2)] 
• 1295-35-8 bis(1,5-cyclooctadiene)nickel ⁽⁰⁾ 
• 1256262-62-0 C₃₄H₃₃BrNiP₂ 
• 108-88-3 toluene 
• 16303-58-5 5,5'-dimethyl-2,2'-dithiophene 

Relevant articles and documents

Nickel-catalyzed electrocarboxylation of allylic halides with CO2

Nickel-catalyzed regioselective electrocarboxylation of allylic halides with CO2at atmospheric pressure has been developed by adjusting reaction parameters, including catalyst, solvent, temperature and additive. β,γ-Unsaturated carboxylic acids were obtained in moderate to good yields and with high chain selectivity. This reaction shows tolerance to functional groups. In addition, cyclic voltammetry was performed to provide the possible mechanism of nickel-catalyzed CO2allylation.

Efficient catalytic transfer hydrogenation reactions of carbonyl compounds by Ni(II)-diphosphine complexes

The catalytic transfer hydrogenation reactions of a series of aromatic and aliphatic carbonyl compounds were investigated using divalent Ni(II)-diphosphine complexes, [L2NiCl2] (where L2 = 1,1-bis(diphenylphosphino)methane (dppm), 1,2-bis(diphenylphosphino)ethane (dppe), 1,3-bis(diphenylphosphino)propane (dppp), 1,1-bis(diphenylphosphino)ferrocene (dppf), and N-butyl-N-(diphenylphosphino)-1,1-diphenylphosphinamine (dppba)). This is a single-step reaction in the presence of potassium hydroxide and isopropyl alcohol to afford the corresponding alcohols. This protocol tolerates other sensitive functional groups like olefinic double bonds and also achieves high chemoselectivity. All the reactions were monitored by GC and GC–MS. The plausible mechanism is also discussed. The method reported in the present article is simple, cost-effective, and provides excellent conversions. Nickel-diphosphine complexes appear as a potential alternative to expensive transition metal complexes.

Process design and scale-up of the synthesis of 2,2′:5′,2′-terthienyl

The objective of this study was the design of a scaleable process for the synthesis of 3-4 mol of α-terthienyl from 2,5-dibromothiophene and thienylmagnesium bromide in a 10-L stirred tank reactor. In THF the Grignard reagent, thienylmagnesium bromide, was readily formed from 2-bromothiophene and magnesium. To avoid crystallization the maximal concentration was limited to 1.4 M. Furthermore, the novel combination of THF and NiCl2[bis(diphenylphosphino)benzene] allows for fast double coupling of the Grignard reagent with 2,5-dibromothiophene. The concentration of catalyst could be limited to 0.5 mol % based on the amount of 2,5-dibromothiophene. An adapted workup procedure was developed, in which n-octane was used to separate the magnesium salts from the desired product. The reaction was performed in a (semi)batch-wise operated reactor. A global model for the coupling step proved to predict the results at 0.1-, 1-, and 10-L scales very accurately. The heat of reaction evolved in the coupling step was valorized and could be handled easily. Mixing of the feed stream and the reactor content proved to be another important factor in the scaling-up of the α-terthienyl synthesis.