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216666
Tetrakis(triphenylphosphine)palladium(0)
99%, solid
Synonym(s):
Palladium-tetrakis(triphenylphosphine), Pd(PPh3)4
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1 G
$43.70
5 G
$126.00
25 G
$540.00
4 X 25 G
$1,740.00
About This Item
Linear Formula:
Pd[(C6H5)3P]4
CAS Number:
Molecular Weight:
1155.56
Beilstein/REAXYS Number:
6704828
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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Product Name
Tetrakis(triphenylphosphine)palladium(0), 99%
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
parameter
air sensitive
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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This Item | 697265 | 8.14761 | 208671 |
|---|---|---|---|
| assay 99% | assay ≥99.99% trace metals basis | assay - | assay 98% |
| reaction suitability core: palladium, reaction type: Heck Reaction, reaction type: Negishi Coupling, reaction type: Stille Coupling, reagent type: catalyst | reaction suitability core: palladium, reaction type: Buchwald-Hartwig Cross Coupling Reaction, 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 suitability - | reaction suitability core: palladium, reaction type: Buchwald-Hartwig Cross Coupling Reaction, 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 |
| form solid | form crystals | form powder | form solid |
| Quality Level 200 | Quality Level 200 | Quality Level 200 | Quality Level 200 |
| storage temp. 2-8°C | storage temp. 2-8°C | storage temp. 2-8°C | storage temp. - |
| parameter air sensitive | parameter - | parameter - | parameter - |
General description
Palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4) iscoordination complex of palladium and is widely used palladium cross-coupling catalyst. These applications include Negishi coupling, Suzuki coupling, Stille coupling, Sonogashira coupling, and Buchwald-Hartwig amination reactions.
Tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) is a commonly used palladium(0) complex in chemical synthesis. It plays a vital role as a catalyst in various organic reactions, especially C-C, C-N, C-O, and C-heteroatom cross-coupling reactions. Pd(PPh3)4 finds extensive application in carbon-carbon bond-forming reactions such as the famous Heck, Suzuki-Miyaura, and Stille reactions. These reactions involve the coupling of aryl, alkyl, or vinyl halides with other organic compounds to yield valuable products. The catalytic cycle involves the oxidative addition of the organic halide to palladium(0), transmetalation with a suitable organometallic reagent or boronic acid, and reductive elimination to form the desired product. Pd(PPh3)4 has also been utilized in various other transformations including allylic substitutions, nucleophilic additions to alkenes and alkynes, and cycloadditions.
Tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) is a commonly used palladium(0) complex in chemical synthesis. It plays a vital role as a catalyst in various organic reactions, especially C-C, C-N, C-O, and C-heteroatom cross-coupling reactions. Pd(PPh3)4 finds extensive application in carbon-carbon bond-forming reactions such as the famous Heck, Suzuki-Miyaura, and Stille reactions. These reactions involve the coupling of aryl, alkyl, or vinyl halides with other organic compounds to yield valuable products. The catalytic cycle involves the oxidative addition of the organic halide to palladium(0), transmetalation with a suitable organometallic reagent or boronic acid, and reductive elimination to form the desired product. Pd(PPh3)4 has also been utilized in various other transformations including allylic substitutions, nucleophilic additions to alkenes and alkynes, and cycloadditions.
Application
Tetrakis(triphenylphosphine)palladium(0) can be used as a catalyst in:
- Negishi coupling[1] (eq. 1), Suzuki coupling[2] (eq. 2), Stille coupling[3] (eq. 3), Sonogashira coupling reaction[4] (eq. 4), and Buchwald-Hartwig amination reaction[5] (eq. 5)
- The carbonylation of vinyl iodides[6] (eq. 6)
- The reduction reaction of aryl bromides[7] (eq. 7)
- Carbon-tin bond formation[8] (eq. 8)
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Warning
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Hazard Classifications
Acute Tox. 4 Oral
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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)
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)
Kotora, M; Xu, C.; Negishi, E.
The Journal of Organic Chemistry, 62, 8957-8957 (1997)
Milstein, D.; Still, J. K.
Journal of the American Chemical Society, 101, 4992-4992 (1979)
Articles
Effective in key synthesis reactions like Knoevenagel condensation, thalidomide synthesis, and Suzuki coupling for sustainable chemical transformations.
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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?
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A change in color of the material indicates oxidation and it will no longer be active as a catalyst.
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