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Merck
CN

222380

Sigma-Aldrich

Allylpalladium(II) chloride dimer

greener alternative

98%

Synonym(s):

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

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About This Item

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

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Quality Level

Assay

98%

form

solid

reaction suitability

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

greener alternative product characteristics

Catalysis
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sustainability

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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

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1 of 4

This Item
497283067442424
Sigma-Aldrich

92716

Atto 620

Atto 700 BioReagent, suitable for fluorescence, ≥90.0% (HPCE)

30674

Atto 700

Sigma-Aldrich

42424

Atto 550

fluorescence

λex 617 nm; λem 641 nm in 0.1 M phosphate pH 7.0

fluorescence

λex 619 nm; λem 643 nm in 0.1 M phosphate pH 7.0

fluorescence

λex 681 nm; λem 714 nm in 0.1 M phosphate pH 7.0

fluorescence

-

form

powder

form

solid

form

-

form

powder

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

assay

≥90% (HPCE)

assay

≥80% (coupling to thiols)

assay

≥90.0% (HPCE)

assay

≥90% (HPLC)

product line

BioReagent

product line

-

product line

BioReagent

product line

-

General description

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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Application

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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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

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Radetich, B.; RajanBabu, T. V.
Journal of the American Chemical Society, 120, 8007-8007 (1998)
An N-heterocyclic carbene-palladium-η3-allyl chloride complex for the Suzuki-Miyaura coupling of aryl halides.
Broekemier NW, et al.
European Journal of Chemistry, 5(1), 162-166 (2014)
Yasuyuki Harada et al.
Organic letters, 7(20), 4385-4387 (2005-09-24)
[reaction: see text] The reaction of yne esters with carbon monoxide (1 atm) in the presence of palladium complexes gives bicyclic unsaturated lactone derivatives in good to high yields. The 2-pyridinyloxy group is a good leaving group among leaving groups
Superhydrophobicity of nanostructured carbon films in a wide range of pH values.
Lin Feng et al.
Angewandte Chemie (International ed. in English), 42(35), 4217-4220 (2003-09-23)
Efficient Heck vinylation of aryl halides catalyzed by a new air-stable palladium-tetraphosphine complex.
M Feuerstein et al.
The Journal of organic chemistry, 66(17), 5923-5925 (2001-08-21)

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.

Protocols

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

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