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14264-16-5

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14264-16-5 Usage

Reaction

Catalyst for hydrosilylation of styrene with diphenysilane Catalyst for carboxylation of various aryl chlorides and other derivatives Catalyst for C–P cross-coupling reactions of diphenylphosphine oxide with aryl chloride Catalyst for N?Heterocyclic carbene-assisted cross-coupling reactions of diarylborinic acids with aryl chlorides,tosylates, and sulfamates. Catalyst for Negishi biaryl ketone synthesis by cross-coupling of amides with aryl zinc halides via carbon-nitrogen bond cleavage.

Chemical Properties

dark green to dark grey crystals or powder

Uses

Different sources of media describe the Uses of 14264-16-5 differently. You can refer to the following data:
1. Coordination compund.
2. suzuki reaction
3. Dichlorobis(triphenylphosphine)nickel(II) is used as a catalyst for cross-coupling of Grignard reagents, hydrosilylations, hydrogenation and polymerization.

Purification Methods

Wash it with glacial AcOH and dry it in a vacuum over H2SO4 and KOH until AcOH is removed. [Venanzi J Chem Soc 719 1958, Kocienski et al. J Org Chem 54 1215 1989, Beilstein 16 IV 953.]

Check Digit Verification of cas no

The CAS Registry Mumber 14264-16-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,2,6 and 4 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 14264-16:
(7*1)+(6*4)+(5*2)+(4*6)+(3*4)+(2*1)+(1*6)=85
85 % 10 = 5
So 14264-16-5 is a valid CAS Registry Number.
InChI:InChI=1/2C18H15P.2ClH.Ni/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;;/h2*1-15H;2*1H;/q;;;;+2

14264-16-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Packaging
  • Price
  • Detail
  • TCI America

  • (B1571)  Bis(triphenylphosphine)nickel(II) Dichloride  >96.0%(T)

  • 14264-16-5

  • 10g

  • 320.00CNY

  • Detail
  • TCI America

  • (B1571)  Bis(triphenylphosphine)nickel(II) Dichloride  >96.0%(T)

  • 14264-16-5

  • 100g

  • 1,450.00CNY

  • Detail
  • Alfa Aesar

  • (13930)  Dichlorobis(triphenylphosphine)nickel(II), 98%   

  • 14264-16-5

  • 10g

  • 354.0CNY

  • Detail
  • Alfa Aesar

  • (13930)  Dichlorobis(triphenylphosphine)nickel(II), 98%   

  • 14264-16-5

  • 50g

  • 1653.0CNY

  • Detail
  • Aldrich

  • (237116)  Bis(triphenylphosphine)nickel(II)dichloride  synthesis grade

  • 14264-16-5

  • 237116-10G

  • 500.76CNY

  • Detail
  • Aldrich

  • (237116)  Bis(triphenylphosphine)nickel(II)dichloride  synthesis grade

  • 14264-16-5

  • 237116-50G

  • 1,781.91CNY

  • Detail
  • Aldrich

  • (529621)  Bis(triphenylphosphine)nickel(II)dichloride  99.99% trace metals basis

  • 14264-16-5

  • 529621-10G

  • 962.91CNY

  • Detail

14264-16-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Bis(triphenylphosphine)nickel(II) Dichloride

1.2 Other means of identification

Product number -
Other names Dichlorobis(triphenylphosphine)nickel(II)

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14264-16-5 SDS

14264-16-5Relevant articles and documents

Corain, Benedetto,Longato, Bruno,Angeletti, Roberto,Valle, Giovanni

, p. 15 - 18 (1985)

On the feasibility of nickel-catalyzed trifluoromethylation of aryl halides

Jover, Jess,Miloserdov, Fedor M.,Benet-Buchholz, Jordi,Grushin, Vladimir V.,Maseras, Feliu

, p. 6531 - 6543 (2014)

A computational screening of 42 bidentate phosphines (PP) has yielded promising candidates for Ph-CF3 reductive elimination from Ni(II) complexes of the type [(PP)Ni(Ph)(CF3)]. The computed barriers and synthetic accessibility consid

Synthesis and biological evaluation of alanine derived bioactive P-toluenesulphonamide analogs

Amasiatu, Ifeanyi S.,Egbujor, Melford C.,Egu, Samuel A.,Egwuatu, Pius I.,Eze, Florence U.,Okoro, Uchechukwu C.

, p. 6449 - 6458 (2020/10/27)

Sulphonamides and carboxamides have great pharmacological importance. The purpose of the study was to synthesize alanine-derived bioactive sulphonamides bearing carboxamides and evaluate their biological activi-ties. The reaction of p-toluenesulphonyl chloride with L-alanine afforded compound 1, which was acetylated to obtain compound 2. The chlorina-tion and ammonolysis of compound 2 gave the carboxamide backbone (3) which was coupled with aryl/heteroaryl halides to afford the hybrid compounds 4, 5 and 6. Structures were confirmed by FTIR,1 H-NMR,13 C-NMR spectra and elemental analytical data. The in vitro antimicrobial properties were determined by agar dilution, and the antioxidant properties were also investigated. Molecular docking interactions of the analogues were determined using PyRx. Compounds 4, 5 and 6 exhibited excellent in vitro antimi-crobial properties in the range of 0.5-1.0mg/ml while compounds 1and 2 had half-maximal inhibitory concentration (IC50) of 1.11±0.15μg/ml and 1.12±0.13μg/ml respectively. For the molecular docking studies, compounds 5 and 6 displayed the best antitrypanosomal activity with binding affinities of-13.95 and-13.51kcal/mol respectively while compound 4 showed the highest in silico antimalarial activity having binding affinity of-11.95kcal/mol. All the alanine derived sulphonamides were observed to be potential antimicrobial, antioxidant, antitrypanosomal and antimalarial agents following the biological activities studies.

Catalysis of Cross-Coupling and Homocoupling Reactions of Aryl Halides Utilizing Ni(0), Ni(I), and Ni(II) Precursors; Ni(0) Compounds as the Probable Catalytic Species but Ni(I) Compounds as Intermediates and Products

Manzoor, Adeela,Wienefeld, Patrick,Baird, Michael C.,Budzelaar, Peter H.M.

, p. 3508 - 3519 (2017/10/03)

Both Ni(0) and Ni(I) compounds are believed to exhibit cross-coupling catalytic properties under various conditions, and the compounds Ni(PPh3)4 and NiCl(PPh3)3 are compared as catalysts for representative Suzuki-Miyaura and Heck-Mizoroki cross-coupling reactions. The Ni(0) compound exhibits catalytic activities, for cross-coupling of chloro and bromoanisole with phenylboronic acid and of bromobenzene with styrene, yielding results which are comparable with those of many palladium-based catalysts, but our findings with NiCl(PPh3)3 are at this point unclear. It seems to convert to catalytically active Ni(0) species under Suzuki-Miyaura reaction conditions and is ineffective for Heck-Mizoroki cross-coupling. The paramagnetic Ni(I) compounds NiX(PPh3)3 (X = Cl, Br, I) are characterized for the first time by 1H NMR spectroscopy and are found to exhibit broad meta and para resonances at δ 9-11 and 3-4, respectively, and very broad ortho resonances at δ 46; these resonances are very useful for detecting Ni(I) species in solution. The chemical shifts of NiCl(PPh3)3 vary with the concentration of free PPh3, with which it exchanges, and are also temperature-dependent, consistent with Curie law behavior. The compound trans-NiPhCl(PPh3)2, the product of oxidative addition of chlorobenzene to Ni(PPh3)4 and a putative intermediate in cross-coupling reactions of chlorobenzene, is found during the course of this investigation to exhibit entirely unanticipated thermal lability in solution in the absence of free PPh3. It readily decomposes to biphenyl and NiCl(PPh3)2 in a reaction relevant to the long-known but little-understood nickel-catalyzed conversion of aryl halides to biaryls. Ni(I) and biphenyl formation is initiated by PPh3 dissociation from trans-NiPhCl(PPh3)2 and formation of a dinuclear intermediate, a process which is now better defined using DFT methodologies.

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