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683396

[Pd(allyl)Cl]2

greener alternative

≥98.0% (C, elemental analysis), solid, Umicore

[Pd(allyl)Cl]2

Synonym(s):

Allylpalladium(II) chloride dimer, Allylchloropalladium dimer, Bis(η3-allyl)di(μ-chloro)dipalladium(II), Bis(allyl)dichlorodipalladium, Bis(allyl)dichloropalladium, Bis(allylchloropalladium), Diallyldichlorodipalladium, [PdCl(C3H5)]2

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Pack SizeSKUAvailabilityPrice
500 mg
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$87.30
5 g
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$606.00

About This Item

Empirical Formula (Hill Notation):
C6H10Cl2Pd2
CAS Number:
Molecular Weight:
365.89
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12161600
EC Number:
234-579-8
Beilstein/REAXYS Number:
4124623
MDL number:

$87.30


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Product Name

[Pd(allyl)Cl]2, Umicore

Quality Level

assay

≥98.0% (C, elemental analysis)

form

solid

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

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

greener alternative category

storage temp.

2-8°C

SMILES string

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

InChI key

TWKVUTXHANJYGH-UHFFFAOYSA-L

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

Application

[Pd(allyl)Cl]2 can be used as a catalyst:
  • For the silylation of organobromides.
  • To synthesize α-aryl carbonyl compounds by coupling reaction between aldehydes and aryl halides.
  • To prepare various arylthiophene derivatives by cross-coupling reaction with aryl halides via C-H functionalization.

Legal Information

Product of Umicore

Additional information available at www.pmc.umicore.com

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This Item
222380720526700045
reaction suitability

core: palladium, reaction type: Cross Couplings, reaction type: Hiyama Coupling, reaction type: Sonogashira Coupling, reaction type: Suzuki-Miyaura Coupling, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Negishi Coupling, reagent type: catalyst, reaction type: Stille Coupling, reaction type: Heck Reaction

reaction suitability

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

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

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

assay

≥98.0% (C, elemental analysis)

assay

98%

assay

97%

assay

≥97%

form

solid

form

solid

form

solid

form

powder

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

sustainability

Greener Alternative Product

sustainability

Greener Alternative Product

sustainability

-

sustainability

-


pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

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



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Articles

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.

Precatalysts for asymmetric catalysis offer batch-to-batch consistency in a range of catalytic reactions, supporting diverse research needs.


Direct Arylation of Thiophenes via Palladium-Catalysed C-H Functionalisation at Low Catalyst Loadings
Battace A, et al.
Advanced Synthesis & Catalysis, 349(16), 2507-2516 (2007)
Synthesis of HOMSi Reagents by Pd/Cu-Catalyzed Silylation of Bromoarenes with Disilanes
Minami Y, et al.
Chemistry Letters (Jpn), 43(2), 201-203 (2014)
Palladium-catalyzed alpha-arylation of aldehydes with bromo- and chloroarenes catalyzed by [{Pd(allyl)Cl}2] and dppf or Q-phos
Giang D Vo and John F Hartwig
Angewandte Chemie (International ed. in English), 2127-2130 (2008)



Global Trade Item Number

SKUGTIN
683396-500MG04061832755724
683396-5G04061832755731

Questions

1–2 of 2 Questions  
  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/418/501/product-dating-information-06-25-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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