Skip to Content
Merck
All Photos(1)

Documents

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

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C18H18Cl2Pd2
CAS Number:
Molecular Weight:
518.08
MDL number:
UNSPSC Code:
12352300
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service