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720526

Sigma-Aldrich

Palladium(π-cinnamyl) chloride dimer

97%

Synonym(s):

Bis[cinnamyl palladium(II) chloride], Palladium(1-phenylallyl)chloride dimer, [(Cinnamyl)PdCl]2, [Pd(1-phenylallyl)Cl]2

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About This Item

Empirical Formula (Hill Notation):
C18H18Cl2Pd2
CAS Number:
12131-44-1
Molecular Weight:
518.08
MDL number:
MFCD16621470
UNSPSC Code:
12161600
PubChem Substance ID:
329763720
NACRES:
NA.22
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Assay

97%

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

mp

218-220 °C

storage temp.

2-8°C

SMILES string

Cl[Pd].Cl[Pd].[CH2][CH][CH]c1ccccc1.[CH2][CH][CH]c2ccccc2

InChI

1S/2C9H9.2ClH.2Pd/c2*1-2-6-9-7-4-3-5-8-9;;;;/h2*2-8H,1H2;2*1H;;/q;;;;2*+1/p-2

InChI key

SHWAPUDBEQXXLQ-UHFFFAOYSA-L

Related Categories

Application

Palladium(π-cinnamyl) chloride dimer can be used as a catalyst for the:
  • Ammonia cross-coupling reactions to synthesize arylamines.[1]
  • Conversion of aryl triflates to fluorides.[2]

It can also be used as a source of palladium in the asymmetric α-arylation of amides.[3]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW3106
MKCT8600
MKCS2753
MKCR2485
MKCP0830

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Evidence for in situ catalyst modification during the Pd-catalyzed conversion of aryl triflates to aryl fluorides.
Maimone TJ, et al.
Journal of the American Chemical Society, 133(45), 18106-18109 (2011)
Matching the chirality of monodentate N-heterocyclic carbene ligands: a case study on well-defined palladium complexes for the asymmetric ?-arylation of amides.
Luan X, et al.
Organic Letters, 10(24), 5569-5572 (2008)
AP, N?Ligand for Palladium?Catalyzed Ammonia Arylation: Coupling of Deactivated Aryl Chlorides, Chemoselective Arylations, and Room Temperature Reactions
Lundgren R J, et al.
Angewandte Chemie (International Edition in English), 122(24), 4165-4168 (2010)

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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