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Sigma-Aldrich

Allylpalladium(II) chloride dimer

greener alternative

98%

Sinonimo/i:

Bis((η3-allyl)(chloro)palladium), Di-ο-allyldi-μ-chlorodipalladium, [PdCl(C3H5)]2

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About This Item

Formula empirica (notazione di Hill):
C6H10Cl2Pd2
Numero CAS:
12012-95-2
Peso molecolare:
365.89
Beilstein:
4124623
Numero CE:
234-579-8
Numero MDL:
MFCD00044874
Codice UNSPSC:
12161600
ID PubChem:
24853328
NACRES:
NA.22
Prezzi e disponibilità al momento non sono disponibili

Livello qualitativo

200

Saggio

98%

Stato

solid

Impiego in reazioni chimiche

core: palladium
reaction type: Cross Couplings
reagent type: catalyst
reaction type: C-H Activation

Caratteristiche più verdi

Catalysis
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sustainability

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Categoria alternativa più verde

, Aligned

Temperatura di conservazione

2-8°C

Stringa SMILE

Cl[Pd]CC=C.Cl[Pd]CC=C

InChI

1S/2C3H5.2ClH.2Pd/c2*1-3-2;;;;/h2*3H,1-2H2;2*1H;;/q;;;;2*+1/p-2
TWKVUTXHANJYGH-UHFFFAOYSA-L

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Descrizione generale

Allylpalladium(II) chloride dimer is employed as catalyst in Heck reaction. It also participates as catalyst in the tandem nucleophilic allylation-alkoxyallylation reaction of the alkynylaldehydes with allyl chloride and allyltributylstannane.[1]
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Applicazioni

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Allylpalladium(II) chloride dimer has been employed for the following studies:
  • Synthesis of cationic palladium cataysts, used in the microwave-assisted Heck arylation.[2]
  • Synthesis of N-heterocyclic carbene-palladium-η3-allyl chloride complexes, which are efficient catalyst for the Suzuki-Miyaura cross-coupling of aryl bromides and activated aryl chlorides.[3]
  • Synthesis of 1,4-diallyl-1,2-dihydroisoquinolines.[4]
  • As catalyst for greener Buchwald-Hartwig coupling in TPGS-750-M.

On the Way Towards Greener Transition-Metal-Catalyzed Processes as Quantified by E Factors

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315

Classi di pericolo

Skin Irrit. 2

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
0000335391
0000335391
MKCS9452
0000287837
MKCT4872

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European Journal of Organic Chemistry, 3122-3122 (2007)
The Journal of Organic Chemistry, 59, 5034-5034 (1994)
Matthias Eckhardt et al.
Journal of the American Chemical Society, 125(45), 13642-13643 (2003-11-06)
A Pd/N-heterocyclic carbene-based catalyst achieves the Sonogashira coupling of an array of functionalized, beta-hydrogen-containing alkyl bromides and iodides under mild conditions. By furnishing the first example of a nonphosphine-based palladium catalyst for cross-coupling unactivated alkyl electrophiles, this study provides an
Synthesis, 1683-1683 (2007)
Suzuki cross-couplings of alkyl tosylates that possess beta hydrogen atoms: synthetic and mechanistic studies.
Matthew R Netherton et al.
Angewandte Chemie (International ed. in English), 41(20), 3910-3912 (2002-10-19)
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Articoli

Palladium-catalyzed Cross-coupling Reactions

A variety of palladium-catalyzed cross-coupling reactions can be run under room temperature conditions in water with TPGS- 750-M, using a variety of commercially available palladium complexes and ligands.

Protocolli

Cross-Coupling Reactions in Water

TPGS-750-M surfactant enables various reactions in water at room temperature, enhancing efficiency and versatility in synthesis.

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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