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939595

[IPr-H]₂Pd₂Cl₆

Name: [IPr-H]2Pd2Cl6
Brand: ALDRICH

≥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

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Properties

Product Name

[IPr-H]₂Pd₂Cl₆, ≥95%

Quality Segment

100

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

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

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

InChI key

QGYYJDLZEPDDDF-UHFFFAOYSA-J

Description

General description

[IPr-H]₂Pd₂Cl₆is 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]₂Pd₂Cl₆compared 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.

pictograms

GHS05,GHS07,GHS09

signalword

Danger

hcodes

H302,H318,H410

pcodes

P264 - P273 - P280 - P301 + P312 - P305 + P351 + P338 - P391

Hazard Classifications

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

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c