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520764

Sigma-Aldrich

乙酸钯(II)

≥99.9% trace metals basis

别名:
Pd(OAc)2
线性分子式:
Pd(OCOCH3)2
CAS号:
分子量:
224.51
Beilstein:
6086766
EC 号:
MDL编号:
PubChem化学物质编号:
NACRES:
NA.22

质量水平

200

测定

≥99.9% trace metals basis

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
reaction type: C-H Activation

mp

216.3-223.7 °C (dec.)

SMILES string

CC(O[Pd]OC(C)=O)=O

InChI

1S/2C2H4O2.Pd/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2

InChI key

YJVFFLUZDVXJQI-UHFFFAOYSA-L

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一般描述

醋酸钯是一种是均相氧化催化剂。它参与烯基和芳香族化合物的活化,使其发生氧化分子间和分子内亲核反应。醋酸钯的晶体为三聚体结构,具有对称性 D3h。晶体中的每个钯原子通过双乙酸酯键与其他两个钯原子连接。在聚脲中对醋酸钯进行微囊化处理,可得到聚脲包裹的醋酸钯。它是一种通用的非均相催化剂,适用于各种无膦交叉偶联反应。它能催化苯酞与不同烯烃的Heck偶联反应。

应用

乙酸钯(II)用作以下反应的催化剂:
  • 烯丙基乙酸酯形成。(反应式1)
  • 三键的氢硒化。(反应式2)
  • 烯烃的Heck芳基化。(反应式3)
  • 环羰基化。(反应式4)
  • Buchwald-Hartwig胺化反应。(反应式5)
Pd(OAc)<SUB>2</SUB> catalyst

包装

1, 5, 25, 100 g in glass bottle

警示用语:

Danger

危险声明

危险分类

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Sens. 1A

储存分类代码

11 - Combustible Solids

WGK

WGK 2

闪点(F)

Not applicable

闪点(C)

Not applicable

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves

分析证书

原产地证书 (CofO)

  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. What reactions are Product 520764, Palladium (II) acetate, used in?

    Palladium (II) acetate is used as a catalyst for a number of reactions, including:  Suzuki coupling reactions, (See ChemFiles 2.1 and ChemFiles 4.2) vinylation, (i.e. the Heck Reaction), rearrangement of acyclic dienes (i.e. the Cope Reaction).Papers that cite the use of this reagent are listed below. 1. B.M. Trost Tet. 33, 2615, (1977)2. R.F. Heck Acc. Chem. Res. 12, 146, (1979)3. Tet. 62, 9002, (2006)4. Org. Lett. 8, 3311, (2006) abstract5. Organometallic News 2, 52, (2002)

  4. What is Product 520764, Palladium (II) acetate, soluble in?

    Palladium acetate is not water-soluble; it is organic soluble. Although Sigma-Aldrich does not test solubility of 520764 directly, it is expected to be soluble in most common organic solvents, like chloroform, methylene chloride and acetone, according to the manufacturer.

  5. When using are Product 520764, Palladium (II) acetate, what can I use to remove traces of palladium that this catalyst may leave behind?

    We would recommend using a metallic scavenger like the QuadraPureTM products. Product numbers 655422 and 657662 are designed to scavenge palladium ions and are effective in both acidic and basic conditions. The resins are capable of removing metallic contamination to very low levels and are ideal for pharmaceutical or fine chemical processing.

  6. What is the difference between Product 520764, Palladium (II) acetate, and the palladium acetate in the form of a ChemDose® tablet?

    The ChemDose® products offer a streamlined way to catalyze reactions. The catalyst is dispersed in an inert tablet matrix in specific millimolar and micromolar quantities. The tablets can decrease time spent on weighing/adding the catalyst to the reaction mixture. The tablets effectively give the same reaction yields with a controlled release of the catalyst. They are also extremely easy to remove after the reaction is complete. The inert tablet usually stays intact throughout the reaction. Product 684929 is the ChemDose® tablet that contains 2.0 μmol of palladium (II) acetate, while product#: 685593 is the 10μmol version. More information on these products can be found at the link below. 

  7. What atmosphere is Product 520764, Palladium (II) acetate, packaged under?

    This material is packaged under a layer of nitrogen to reduce the chance of moisture contamination.

  8. 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.

  9. 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. 

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

    Ask a Scientist here.

A Facile Synthesis of Novel Cyclic Esters of γ-Keto Acid Derivatives by Heck Coupling Reaction.
ShashiKumar ND, et al.
Journal of Heterocyclic Chemistry, 51(S1), E354-E357 (2014)
Brunner, M.; Alper, H
The Journal of Organic Chemistry, 62, 7565-7565 (1997)
Wolfe, J. P.; Buchwald, S. L.
The Journal of Organic Chemistry, 62, 1264-1264 (1997)
Palladium (II) Acetate
Grennberg H, et al.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2015)
The crystal structure of Trimeric palladium (II) acetate.
Skapski AC and Smart ML.
Journal of the Chemical Society. Chemical Communications, 11, 658b-6659 (1970)

技术文章

Heck Reaction Applications & Products

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes and aryl or vinyl halides (or triflates) to afford substituted alkenes.

相关内容

Heck反应

Heck反应是烯烃与芳基或乙烯基卤化物(或三氟甲磺酸酯)之间的钯催化交叉偶联反应,用于生成取代的烯烃。

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