1,2-Bis(diphenylphosphino)ethane nickel(II) chloride

Base Information

• Chemical Name: 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride
• CAS No.: 14647-23-5
• Molecular Formula: C26H24Cl2NiP2
• Molecular Weight: 528.02
• Hs Code.: 29319090
• European Community (EC) Number: 629-489-4
• DSSTox Substance ID: DTXSID60432121
• Wikipedia: Dichloro(1,2-bis(diphenylphosphino)ethane)nickel
• Wikidata: Q66724799
• Mol file: 14647-23-5.mol

Synonyms:1,2-Bis(diphenylphosphino)ethane nickel(II) chloride;14647-23-5;2-diphenylphosphanylethyl(diphenyl)phosphane;nickel(2+);dichloride;1,2-Bis(diphenylphosphinoethane)nickel(II) chloride;Dichloro[1,2-bis(diphenylphosphino)ethane]nickel(II);[1,2-Bis(diphenylphosphino)ethane]nickel(II) Dichloride;DTXSID60432121;AMY19685;BCP22511;AKOS015915194;nickel(2+) ion [2-(diphenylphosphanyl)ethyl]diphenylphosphane dichloride;AC-4981;CS-W002089;DS-0824;B2225;1,2-Ethylenebis(diphenylphosphine)nickel dichloride

Chemical Property of 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride

Chemical Property:

• Appearance/Colour: Orange to red crystalline powder
• Vapor Pressure: 3.38E-10mmHg at 25°C
• Melting Point: 263-265 °C(lit.)
• Boiling Point: 514.8 °C at 760 mmHg
• Flash Point: 281.7 °C
• PSA: 27.18000
• LogP: -0.73980
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Methanol (Sparingly)
• Water Solubility.: insoluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 526.008372
• Heavy Atom Count: 31
• Complexity: 336

Purity/Quality:

99% ^*data from raw suppliers

[Bis(diphenylphosphino)ethane]dichloronickel ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xn
• Hazard Codes: T,Xn
• Statements: 45-20/21/22-36/37/38-42/43-40
• Safety Statements: 53-22-26-36-45-52

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(CCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.[Cl-].[Cl-].[Ni+2]
• Uses: suzuki reaction Dichloro[bis(1,2-diphenylphosphino)ethane]nickel(II) is a reactant involved in Kumada catalyst-transfer polycondensation, oxidation of carboranyl phosphine ligands, synthesis of nickel-iron dithiolato hydrides, Ullmann reactions - homocoupling reactions, co-catalyst for hydroformylation of alcohols for the synthesis of quaternary carbon centers, catalyst for Wacker-type intramolecular aerobic oxidative amination of alkenes.

Technology Process of 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride

There total 35 articles about 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride 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: 98.0%

nickel(II) chloride hexahydrate + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5)

Guidance literature:

In ethanol; at 80 ℃; for 0.5h; Sealed tube; Inert atmosphere;

DOI:10.1021/om500156q

Reference yield: 98.0%

→ cis-[NiCl2(1,2-bis(diphenylphosphino)ethane)] (14647-23-5)

Guidance literature:

In ethanol; at 80 ℃; for 0.5h; Inert atmosphere;

Reference yield: 96.0%

(1,2-bis(diphenylphosphino)ethane)Ni(C2H4CO2) + chlorine (7782-50-5) → 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + 3-chloropropionic anhydride (20495-99-2) + [(1,2-bis(diphenylphosphino)ethaneO2)3Ni][NiCl4]

Guidance literature:

In dichloromethane; at -196.16 ℃; for 14h; Glovebox; Sealed tube;

DOI:10.1002/ejic.201402952

upstream raw materials:

trans-1,2-bis(diphenylphosphino)ethylene

hydrogenchloride

Ni⁽⁰⁾(1,2-bis(diphenylphosphino)ethane)2

dichloronickel(1,2-dimethoxyethane)

Downstream raw materials:

7-isopropylindene

1-(6'-methoxy-2'-naphthyl)-propane

Ni⁽⁰⁾(1,2-bis(diphenylphosphino)ethane)2

(((C₆H₅)2PCH₂CH₂P(C₆H₅)2)Ni(PSi(CH₃)3)2)

Refernces

Nickel-catalyzed cross-coupling of neopentyl arenesulfonates with methyl and primary alkylmagnesium bromides

10.1021/jo048300c

The research explores a novel method for the synthesis of alkylarenes using nickel-catalyzed cross-coupling reactions. The study aims to develop an efficient and chemoselective approach for substituting sulfur-containing groups in aromatic compounds, which could serve as an alternative to traditional methods involving halides and triflates. The researchers used neopentyl arenesulfonates as the electrophilic components and reacted them with methyl and primary alkylmagnesium bromides in the presence of the nickel catalyst dppeNiCl2. The reactions were carried out in refluxing tetrahydrofuran (THF) and resulted in the formation of the corresponding alkylarenes in good yields. The study concludes that the alkyloxysulfonyl group is a suitable alternative to halides and triflates in certain situations, particularly when a leaving group that is inert to palladium catalysts but reactive with nickel catalysts is needed. This method offers a versatile and efficient route for the synthesis of alkylarenes, with potential applications in organic synthesis and solid-phase organic synthesis.