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Merck
CN

216666

Sigma-Aldrich

四(三苯基膦)钯(0)

99%

别名:

Pd(PPh3)4, 四(三苯基膦)钯

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About This Item

线性分子式:
Pd[(C6H5)3P]4
CAS号:
分子量:
1155.56
Beilstein:
6704828
EC 号:
MDL编号:
UNSPSC代码:
12352103
PubChem化学物质编号:
NACRES:
NA.22

质量水平

方案

99%

表单

solid

反应适用性

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

参数

air sensitive

储存温度

2-8°C

SMILES字符串

[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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相关类别

一般描述

四(三苯基膦)钯(Pd(PPh3)4)是钯的配位络合物,是应用广泛的钯交叉偶联催化剂。这些应用包括Negishi偶联、Suzuki偶联、Stille偶联、Sonogashira偶联和Buchwald-Hartwig胺化反应。




四(三苯基膦)钯(0)(Pd(PPh3)4)是化学合成中常用的钯(0)配合物。在各种有机反应中,特别是C-C、C-N、C-O和C-杂原子交叉偶联反应,它作为催化剂起着至关重要的作用。Pd(PPh3)4广泛应用于碳-碳键形成反应,例如著名的Heck、Suzuki-Miyaura和Stille反应。这些反应涉及芳基、烷基或乙烯基卤化物与其他有机化合物偶联,产生有价值的产物。催化循环包括将有机卤化物氧化加成到钯(0)中,用合适的有机金属试剂或硼酸进行转移金属化,以及还原消除以形成所需产物。Pd(PPh3)4还用于其他多种转化,包括烯丙基取代、烯烃和炔烃的亲核加成以及环加成。

应用

四(三苯基膦)钯(0)可用作以下反应的催化剂:



  • Negishi偶联反应(反应式1), 铃木偶联反应(反应式2),Stille偶联反应(反应式3),以及Sonogashira偶联反应(反应式4),以及Buchwald-Hartwig氨基化反应(反应式5)
  • 碘化乙烯的羰基化反应(反应式6)
  • 芳基溴化物的还原反应(反应式7)
  • 碳-锡键形成反应(反应式8)
Triphenyl Phosphine Catalyst

象形图

Exclamation mark

警示用语:

Warning

危险声明

危险分类

Acute Tox. 4 Oral

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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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.

  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. 

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    Ask a Scientist here.

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)
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
Miyaura, M.; Suzuki, A.
Journal of the American Chemical Society, 107, 972-972 (1985)
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)

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