216666

Sigma-Aldrich

Tetrakis(triphenylphosphine)palladium(0)

99%

Synonym(s):
Pd(PPh3)4, Palladium-tetrakis(triphenylphosphine)
Linear Formula:
Pd[(C6H5)3P]4
CAS Number:
Molecular Weight:
1155.56
Beilstein/REAXYS Number:
6704828
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

reaction suitability

core: palladium
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: catalyst
reaction type: Buchwald-Hartwig Cross Coupling Reaction

storage temp.

2-8°C

SMILES string

[Pd].c1ccc(cc1)P(c2ccccc2)c3ccccc3.c4ccc(cc4)P(c5ccccc5)c6ccccc6.c7ccc(cc7)P(c8ccccc8)c9ccccc9.c%10ccc(cc%10)P(c%11ccccc%11)c%12ccccc%12

InChI

1S/4C18H15P.Pd/c4*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;/h4*1-15H;

InChI key

NFHFRUOZVGFOOS-UHFFFAOYSA-N

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Application

Tetrakis(triphenylphosphine)palladium(0) can be used as a catalyst in:
  • Negishi coupling (eq. 1), Suzuki coupling (eq. 2), Stille coupling (eq. 3), Sonogashira coupling reaction (eq. 4), and Buchwald-Hartwig amination reaction (eq. 5)
  • The carbonylation of vinyl iodides (eq. 6)
  • The reduction reaction of aryl bromides (eq. 7)
  • Carbon-tin bond formation (eq. 8)
Triphenyl Phosphine Catalyst

Packaging

1, 5, 25, 4×25 g in glass bottle

pictograms

Exclamation mark

signalword

Warning

hazcat

Acute Tox. 4 Oral - Aquatic Chronic 4 - Skin Sens. 1

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

  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.

  3. The color of Product 216666, Pd tetrakis(triphenylphosphine)Cl was a yellow or gold color, but now my material has turned a tan, brown, or green color.  Is it still good to use?

    A change in color of the material indicates oxidation and it will no longer be active as a catalyst.

  4. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

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    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. 

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Hong-Lei Xu et al.
Nature communications, 11(1), 5286-5286 (2020-10-22)
Sandwich-type clusters with the planar fragment containing a heterometallic sheet have remained elusive. In this work, we introduce the [K(2,2,2-crypt)]4{(Ge9)2[η6-Ge(PdPPh3)3]} complex that contains a heterometallic sandwich fragment. The title compound is structurally characterized by means of single-crystal X-ray diffraction, which...
Alami, F.; Ferri, F. et al.
Tetrahedron Letters, 34, 6403-6403 (1993)
Azizian, H.; Eaborn, C.; Pidcock, A.
Journal of Organometallic Chemistry, 215, 49-49 (1981)
Kotora, M; Xu, C.; Negishi, E.
The Journal of Organic Chemistry, 62, 8957-8957 (1997)
Miyaura, M.; Suzuki, A.
Journal of the American Chemical Society, 107, 972-972 (1985)
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