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Merck
CN

939595

[IPr-H]2Pd2Cl6

≥95%, powder or crystals

Synonym(s):

Bis-(1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium)-hexachloropalladate, NHC palladium

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About This Item

Empirical Formula (Hill Notation):
C54H74Cl6N4Pd2
CAS Number:
2417402-64-1
Molecular Weight:
1204.75
PubChem Substance ID:
32347246
NACRES:
NA.21
Assay:
≥95%
Form:
powder or crystals

Key Documents

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Product Name

[IPr-H]2Pd2Cl6, ≥95%

InChI key

QGYYJDLZEPDDDF-UHFFFAOYSA-J

InChI

InChI=1S/2C27H37N2.4ClH.2Cl.2Pd/c2*1-18(2)22-11-9-12-23(19(3)4)26(22)28-15-16-29(17-28)27-24(20(5)6)13-10-14-25(27)21(7)8;;;;;;;;/h2*9-21H,1-8H3;4*1H;;;;/q2*+1;;;;;;;2*+2/p-4

SMILES string

CC(C(C=CC=C1C(C)C)=C1N2C=C[N+](C3=C(C=CC=C3C(C)C)C(C)C)=C2)C.Cl[Pd]4(Cl)[ClH][Pd](Cl)(Cl)[ClH]4.CC(C(C=CC=C5C(C)C)=C5N6C=C[N+](C7=C(C=CC=C7C(C)C)C(C)C)=C6)C

assay

≥95%

form

powder or crystals

reaction suitability

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

color

brown to orange

Quality Level

100

General description

[IPr-H]2Pd2Cl6 is an ionic tetrachloropalladate complex containing 2 equivalents of the cationic imadazolium ligand 1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium.

Application

Upon treatmeant with a suitable base, a catalytically active Pd-NHC complex can be generated in-situ. Suitable for use in difficult Suzuki-Miyaura and Buchwald-Hartwig cross-couplings reactions of aryl chlorides, and trans-amidation cross-coupling reactions of esters and amides.
New NHC-Pd complexes for the cross-coupling of challenging aryl chlorides


Features and Benefits

[IPr-H]2Pd2Cl6 offers similar or greater performance to other similar Pd-NHC precatalysts available while offering several major advatages:
  • The precatalyst avoids the use of ′throw away′ stabilizing ligands often used in similar Pd-NHC complexes.
  • The more sustainable synthesis of [IPr-H]2Pd2Cl6 compared to similar Pd-NHC complexes makes the product a more sustainable choice.
  • A competitive price, with a higher Pd percentage than other Pd-NHC catalysts.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW5785

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Sébastien G Guillet et al.
Chemical communications (Cambridge, England), 56(44), 5953-5956 (2020-04-30)
The reaction mechanism leading to the formation of cross-coupling palladium pre-catalysts of the PEPPSI family was investigated. Two intermediates were isolated and proved to be both suitable synthons to the pre-catalysts, with one permitting the design of a novel and

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