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Bis(triphenylphosphine)nickel(II)chloride

Base Information Edit
  • Chemical Name:Bis(triphenylphosphine)nickel(II)chloride
  • CAS No.:14264-16-5
  • Molecular Formula:C36H30Cl2NiP2
  • Molecular Weight:654.18
  • Hs Code.:29310095
  • European Community (EC) Number:238-154-8
  • Mol file:14264-16-5.mol
Bis(triphenylphosphine)nickel(II)chloride

Synonyms:Dichloronickel - triphenylphosphine (1:2);nickel(2+) chloride - triphenylphosphane (1:2:2);

Suppliers and Price of Bis(triphenylphosphine)nickel(II)chloride
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • Bis(triphenylphosphine)nickel(II) Dichloride
  • 50g
  • $ 110.00
  • TCI Chemical
  • Bis(triphenylphosphine)nickel(II) Dichloride >96.0%(T)
  • 100g
  • $ 169.00
  • TCI Chemical
  • Bis(triphenylphosphine)nickel(II) Dichloride >96.0%(T)
  • 10g
  • $ 36.00
  • Strem Chemicals
  • Bis(triphenylphosphine)nickel(II) chloride, 99%
  • 5g
  • $ 22.00
  • Strem Chemicals
  • Bis(triphenylphosphine)nickel(II) chloride, 99%
  • 25g
  • $ 72.00
  • Sigma-Aldrich
  • Bis(triphenylphosphine)nickel(II) dichloride synthesis grade
  • 10g
  • $ 44.20
  • Sigma-Aldrich
  • Bis(triphenylphosphine)nickel(II) dichloride synthesis grade
  • 50g
  • $ 147.00
  • Sigma-Aldrich
  • Bis(triphenylphosphine)nickel(II) dichloride 99.99% trace metals basis
  • 10g
  • $ 42.70
  • Rare Earth Products
  • Bis(triphenylphosphine)nickel(II)chloride
  • 25gm
  • $ 39.00
  • Rare Earth Products
  • Bis(triphenylphosphine)nickel(II)chloride
  • 100gm
  • $ 145.00
Total 154 raw suppliers
Chemical Property of Bis(triphenylphosphine)nickel(II)chloride Edit
Chemical Property:
  • Appearance/Colour:dark gray solid 
  • Melting Point:250 °C (dec.)(lit.) 
  • Boiling Point:360 °C at 760 mmHg 
  • Flash Point:181.7 °C 
  • PSA:27.18000 
  • LogP:4.04770 
  • Storage Temp.:Store below +30°C. 
  • Sensitive.:Hygroscopic 
  • Solubility.:DMSO (Slightly), Methanol (Slightly) 
  • Water Solubility.:insoluble 
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:2
  • Rotatable Bond Count:6
  • Exact Mass:652.055322
  • Heavy Atom Count:41
  • Complexity:202
Purity/Quality:

99% *data from raw suppliers

Bis(triphenylphosphine)nickel(II) Dichloride *data from reagent suppliers

Safty Information:
  • Pictogram(s): Toxic
  • Hazard Codes:
  • Statements: 45-43-52/53-34-20/21/22 
  • Safety Statements: 53-36/37-45-60-36/37/39-26 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Chemical Classes:Metals -> Metals, Organic Compounds
  • 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.[Cl-].[Cl-].[Ni]
  • General Description Bis(triphenylphosphine)nickel(II) chloride (Ni(PPh3)2Cl2) is a versatile nickel catalyst used in various organic transformations, including the 1,4-addition of arylboronic acids to α,β-unsaturated substrates, stereo- and regioselective cis-hydrophosphorylation of 1,3-enynes under visible-light irradiation, and the synthesis of multi-substituted allenes via nickel-catalyzed SN2' reactions. It functions effectively in conjunction with ligands such as BFBED or 1,10-phenanthroline and can operate under mild conditions, often without requiring a base. The catalyst demonstrates broad substrate tolerance, high selectivity, and good to excellent yields, making it a valuable alternative to noble metal catalysts in cross-coupling and functionalization reactions.
Technology Process of Bis(triphenylphosphine)nickel(II)chloride

There total 31 articles about Bis(triphenylphosphine)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:
Guidance literature:
In neat (no solvent); byproducts: triphenylphosphine; Ar-atmosphere; 140-180°C, 1 h; extn. (ether, CH2Cl2, H2O), evapn. of extract;
DOI:10.1016/S0020-1693(00)90496-1
Guidance literature:
In ethanol; at 80 ℃; for 1h; Sealed tube; Inert atmosphere;
DOI:10.1021/om500156q
Refernces Edit

Catalyzation of 1,4-additions of arylboronic acids to α,β- unsaturated substrates using nickel(I) complexes

10.1016/j.tetlet.2014.02.046

The study presents an innovative method for the 1,4-addition of arylboronic acids to α,β-unsaturated substrates using nickel(I) complexes as catalysts. The nickel(I) species were generated in situ from Ni(PPh3)2Cl2 with the aid of activated iron, and the catalytic system was combined with NN'-bis(4-fluorobenzylidene) ethane-1,2-diamine (BFBED). The reaction is completed without the need for a base, but the presence of potassium iodide is essential. The study suggests a possible Ni(I)–Ni(III) catalytic cycle mechanism and demonstrates the efficiency of the method with yields up to 76%. The scope of the reaction was explored with various substrates and arylboronic acids, showing no significant influence from electron-withdrawing or electron-donating groups. The work provides a valuable contribution to the field of cross-coupling reactions, offering a more environmentally benign and cost-effective alternative to traditional noble metal catalysts.

Stereo- And Regioselective cis-Hydrophosphorylation of 1,3-Enynes Enabled by the Visible-Light Irradiation of NiCl2(PPh3)2

10.1021/acs.orglett.1c00626

The research focuses on the development of a stereo- and regioselective cis-hydrophosphorylation reaction of 1,3-enynes using visible-light irradiation of NiCl2(PPh3)2 as a catalyst. This reaction provides access to a variety of 1,3-dienes with good isolated yields. The experiments involved the use of NiCl2(PPh3)2, 1,10-phenanthroline as a ligand, Cs2CO3 as a base, and MeOH as a solvent. The reaction conditions were optimized to achieve the best yield of the desired (E)-1,3-diene products. Various 1,3-enynes and phosphine oxides were tested to establish the scope of the reaction. Analytical techniques such as NMR spectroscopy and X-ray crystallography were employed to determine the product yields, configurations, and structures. Preliminary mechanistic studies, including deuteration experiments and radical initiator tests, suggested a radical reaction pathway involving the generation of nickel phosphine species and their addition to the C≡C bond of the 1,3-enynes, followed by protonation to yield the cis-hydrophosphorylation products.

Synthesis of multi-substituted allenes from organoalane reagents and propargyl esters by using a nickel catalyst

10.1039/c8ob00781k

The research focuses on the development of a highly efficient and straightforward method for the synthesis of multi-substituted allenes, which are important structural motifs found in natural and pharmaceutical products and serve as building blocks for various organic transformations. The study utilizes a nickel-catalyzed SN2' substitution reaction of propargyl esters with organic aluminum reagents under mild conditions, yielding multi-substituted allenes with good to excellent yields (up to 92%) and high selectivities (up to 99%). The chemicals involved in this process include nickel catalysts such as Ni(PPh3)2Cl2, phosphine ligands like PPh3, organic aluminum reagents such as AlMe3, and a variety of propargyl esters, which bear different substituents like electron-donating or electron-withdrawing groups, thienyl, pyridyl, and alkyl groups. The methodology provides a useful procedure for the synthesis of tri- and tetra-substituted allenes and demonstrates good tolerance for different propargyl esters. The research concludes that the developed method is effective for the synthesis of allenes and is currently exploring the application of this catalyst to other organoaluminum reagents and propargyl esters.

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