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Merck
CN

720526

Palladium(π-cinnamyl) chloride dimer

97%, solid

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
UNSPSC Code:
12161600
PubChem Substance ID:
329763720
NACRES:
NA.22
MDL number:
MFCD16621470

Key Documents

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Product Name

Palladium(π-cinnamyl) chloride dimer, 97%

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

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

Quality Level

100

Related Categories

Application

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

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

Storage Class

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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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)
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)
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)

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