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重要文件

520764

Sigma-Aldrich

乙酸钯(II)

≥99.9% trace metals basis

同義詞:

Pd(OAc)2

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About This Item

線性公式:
Pd(OCOCH3)2
CAS號碼:
分子量::
224.51
Beilstein:
6086766
EC號碼:
MDL號碼:
分類程式碼代碼:
12161600
PubChem物質ID:
NACRES:
NA.22
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品質等級

化驗

≥99.9% trace metals basis

反應適用性

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 type: C-H Activation

mp

216.3-223.7 °C (dec.)

SMILES 字串

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 密鑰

YJVFFLUZDVXJQI-UHFFFAOYSA-L

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相關類別

一般說明

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。[1]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。[2]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。[3]它能催化苯酞与不同烯烃的Heck偶联反应。[4]

應用

醋酸钯被用作下列反应的催化剂:
  • 烯丙基乙酸酯的形成。[5](eq.1)
  • 三键的氢硒化。[6](eq.2)
  • 烯烃的Heck芳基化。[7](eq.3)
  • 环羰基化。[8](eq.4)
  • Buchwald-Hartwig胺化反应。[9](eq.5)
Pd(OAc)<sub>2</sub> catalyst
对于小规模和高通量应用,可选用ChemBeads形式(924377)

相關產品

產品號碼
描述
訂價

訊號詞

Danger

危險聲明

危險分類

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

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 2

閃點(°F)

Not applicable

閃點(°C)

Not applicable

個人防護裝備

dust mask type N95 (US), Eyeshields, Gloves


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存取文件庫

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)-catalyzed C-H bond arylation of electron-deficient arenes at room temperature.
Matthew J Tredwell et al.
Angewandte Chemie (International ed. in English), 50(5), 1076-1079 (2011-01-27)
The crystal structure of Trimeric palladium (II) acetate.
Skapski AC and Smart ML.
Journal of the Chemical Society. Chemical Communications, 11, 658b-6659 (1970)

文章

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。

Questions

1–6 of 6 Questions  
  1. When using are Product 520764, Palladium (II) acetate, what can I use to remove traces of palladium that this catalyst may leave behind?

    1 answer
    1. 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.

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

    1 answer
    1. 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)

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

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

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

    1 answer
    1. 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.

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

    1 answer
    1. 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.

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  6. What is the Department of Transportation shipping information for this product?

    1 answer
    1. 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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