Tetrakis(triphenylphosphine)nickel

Base Information

• Chemical Name: Tetrakis(triphenylphosphine)nickel
• CAS No.: 15133-82-1
• Molecular Formula: 4(C18H15P)^.Ni;C72H60NiP4
• Molecular Weight: 1107.85
• Hs Code.: 29319090
• European Community (EC) Number: 626-363-0
• DSSTox Substance ID: DTXSID50475103
• Mol file: 15133-82-1.mol

Synonyms:15133-82-1;TETRAKIS(TRIPHENYLPHOSPHINE)NICKEL;Tetrakis(triphenylphosphine)nickel(0);nickel;triphenylphosphane;Ni(PPh3)4;Nickel, tetrakis(triphenylphosphine)-, (T-4)-;MFCD00010011;DTXSID50475103;AMY19688;AKOS015914806;SC10022;Tetrakis(triphenylphosphine)nickel (0);FT-0696281;D82226;Tetrakis(triphenylphosphine)nickel(0), Ni 4-7 % (approx.);NI(PPH3)4;NICKEL-TETRAKIS(TRIPHENYLPHOSPHINE);TETRAKIS(TRIPHENYLPHOSPHINE)NICKEL(0)

Chemical Property of Tetrakis(triphenylphosphine)nickel

Chemical Property:

• Vapor Pressure: 4.74E-05mmHg at 25°C
• Melting Point: 123-128°C
• Boiling Point: 360 °C at 760 mmHg
• Flash Point: 181.7 °C
• PSA: 54.36000
• LogP: 13.77920
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: Insoluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 12
• Exact Mass: 1106.299892
• Heavy Atom Count: 77
• Complexity: 202

Purity/Quality:

97% ^*data from raw suppliers

Tetrakis(triphenylphosphine)nickel(0) Ni 4-7 % (approx.) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,F
• Statements: 40-43-11
• Safety Statements: 36/37-36-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Ni]
• Uses: Tetrakis(triphenylphosphine)nickel(0) is a catalyst for coupling reactions of organic halides, organometallic compounds and also for the cyclooligomerization of cumulenes. Catalyst for coupling reactions of organic halides, organometallic Compounds and also for the cyclooligomerization of cumulenes;.

Technology Process of Tetrakis(triphenylphosphine)nickel

There total 44 articles about Tetrakis(triphenylphosphine)nickel 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: 96.0%

η1,η3-octadienediylnickeltriphenylphosphine → tetrakis(triphenylphosphine)nickel(0) (15133-82-1)

Guidance literature:

With triphenylphosphine; In diethyl ether; byproducts: 1,3-butadiene; under Ar; -10°C, excess of P(C6H5)3;

DOI:10.1016/0022-328X(85)87007-8

Reference yield: 82.0%

triphenylphosphine (603-35-0) + nickel dichloride (83864-14-6) → tetrakis(triphenylphosphine)nickel(0) (15133-82-1)

Guidance literature:

With zinc; In N,N-dimethyl-formamide; at 55 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.organomet.1c00265

Reference yield: 80.0%

C12H18Ni → tetrakis(triphenylphosphine)nickel(0) (15133-82-1)

Guidance literature:

With triphenylphosphine; In diethyl ether; byproducts: cyclododecatriene-1,5,9; excess of P(C6H5)3; 0°C;

upstream raw materials:

nickelocene

bis(1,5-cyclooctadiene)nickel ⁽⁰⁾

triphenylphosphine

nickel dichloride

Downstream raw materials:

ethene

4-ethenylcyclohexene

nickel diacetate

cyclo-octa-1,5-diene

Refernces

Ni-catalyzed mild arylation of α-halocarbonyl compounds with arylboronic acids

10.1021/ol702456z

The research focuses on the development of a Ni-catalyzed mild arylation process for the direct arylations of α-halocarbonyl compounds, including esters, amides, and ketones, with various arylboronic acids. The purpose of this study was to create a method that is complementary to the well-established Buchwald?Hartwig approach, offering greater synthetic flexibility and functional group tolerance. The researchers discovered that Ni(PPh3)4 served as a highly effective catalyst, leading to the formation of a wide variety of arylated carbonyl compounds with good to excellent yields. Compared to Pd-catalyzed arylations using aryl halides, the Ni-based catalysis approach demonstrated advantages in terms of functional group tolerance and reaction selectivity. Key chemicals used in the process include α-halocarbonyl compounds, arylboronic acids, and Ni(PPh3)4 as the catalyst, with K3PO4 as a base. The method was found to be simple, general, and practical, holding promise for the preparation of structurally diverse arylated carbonyl compounds.