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216666

Sigma-Aldrich

Tetrakis(triphenylphosphine)palladium(0)

99%

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

Assay

99%

form

solid

reaction suitability

core: palladium
reaction type: Cross Couplings
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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

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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  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.

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Alami, F.; Ferri, F. et al.
Tetrahedron Letters, 34, 6403-6403 (1993)
Kotora, M; Xu, C.; Negishi, E.
The Journal of Organic Chemistry, 62, 8957-8957 (1997)
Azizian, H.; Eaborn, C.; Pidcock, A.
Journal of Organometallic Chemistry, 215, 49-49 (1981)
Miyaura, M.; Suzuki, A.
Journal of the American Chemical Society, 107, 972-972 (1985)
Milstein, D.; Still, J. K.
Journal of the American Chemical Society, 101, 4992-4992 (1979)

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.

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