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529621

Sigma-Aldrich

Bis(triphenylphosphine)nickel(II) dichloride

99.99% trace metals basis

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Synonym(s):
NiCl2(PPh3)2, Dichlorobis(triphenylphosphine)nickel(II), Nickel(II)bis(triphenylphosphine) dichloride
Linear Formula:
[(C6H5)3P]2NiCl2
CAS Number:
14264-16-5
Molecular Weight:
654.17
EC Number:
238-154-8
MDL number:
MFCD00009592
UNSPSC Code:
12352300
PubChem Substance ID:
24877695
NACRES:
NA.23

Assay

99.99% trace metals basis

form

powder or crystals

reaction suitability

core: nickel

mp

250 °C (dec.) (lit.)

SMILES string

Cl[Ni]Cl.c1ccc(cc1)P(c2ccccc2)c3ccccc3.c4ccc(cc4)P(c5ccccc5)c6ccccc6

InChI

1S/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/p-2

InChI key

ZBRJXVVKPBZPAN-UHFFFAOYSA-L

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Application

Ni(PPh3)2Cl2 may be used to undertake nickel assisted phosphination of biaryl O,N triflates with chlorodiphenylphosphine.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H317,H350,H412

Hazard Classifications

Aquatic Chronic 3 - Carc. 1B - Skin Sens. 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

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  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. What are some uses for Bis(triphenylphosphine)nickel(II) dichloride, product 529621?

    Bis(triphenylphosphine)nickel(II) dichloride can be used for the following:1. Precatalyst for the nickel-catalyzed substitution of allylic carbonates with aryl and alkenyl borates.2. Efficient catalyst for the Suzuki coupling of aryl chlorides.3. Catalyst for the three-component synthesis of 1,4-dienes from allenes, vinyl/aryl iodides and alkenylzirconium reagents.4. Catalyst for the β-selective hydroalumination of terminal alkynes.5. Catalyst for the C-P cross-coupling reaction of arylnitriles.

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Chelating Retardation Effect in Nickel Assisted Phosphination: Syntheses of Atropisomeric P,N Ligands
Kwong FY, et al.
Tetrahedron, 56(45), 8893-8899 (2000)

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