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939609

[SIPr-H]2Pd2Cl6

powder or crystals

Sustainability features

Synonym(s):

Bis-(1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium)-hexachloropalladate

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About This Item

Empirical Formula (Hill Notation):
C54H78Cl6N4Pd2
CAS Number:
1802596-02-6
Molecular Weight:
1208.78
NACRES:
NA.21
eCl@ss:
32150319
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Product Name

[SIPr-H]2Pd2Cl6,

form

powder or crystals

Quality Segment

reaction suitability

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

sustainability

Sustainability features

color

brown to orange

greener alternative category

SMILES string

CC(C(C=CC=C1C(C)C)=C1N2CC[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)=C5N6CC[N+](C7=C(C=CC=C7C(C)C)C(C)C)=C6)C

InChI

InChI=1S/2C27H39N2.4ClH.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*9-14,17-21H,15-16H2,1-8H3;4*1H;;;;/q2*+1;;;;;;;2*+2/p-4

InChI key

WHCUDDZJJCQTRX-UHFFFAOYSA-J

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Green Chemistry. Click here for more information.
[SIPr-H]2Pd2Cl6 is an ionic tetrachloropalladate complex containing 2 equivalents of the cationic imadazolium ligand 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-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.

Features and Benefits

[SPr-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 [SIPr-H]2Pd2Cl6 compared to similar Pd-NHC complexes makes the product a more sustainable choice.
  • A competitive price, with a higher Pd percentage than many other Pd-NHC catalysts.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Codes

H302,H319,H411

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2

Storage Class

11 - Combustible Solids

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

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