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

Signal Word

Warning

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

  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.

  5. 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. 

  6. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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    Ask a Scientist here.

Azizian, H.; Eaborn, C.; Pidcock, A.
Journal of Organometallic Chemistry, 215, 49-49 (1981)
Milstein, D.; Still, J. K.
Journal of the American Chemical Society, 101, 4992-4992 (1979)
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)
Palladium-catalyzed formylation of organic halides with carbon monoxide and tin hydride.
V P Baillargeon et al.
Journal of the American Chemical Society, 108(3), 452-461 (1986-02-01)
Articles
A variety of transition-metal catalysts for the Suzuki coupling reaction are now available in our catalog. The majority of these catalysts are palladium- and nickelbased, typically utilizing phosphine-derived ligands.
Read More

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