939595

[IPr-H]₂Pd₂Cl₆

≥95%

• Synonym(s): Bis-(1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium)-hexachloropalladate, NHC palladium
• Empirical Formula (Hill Notation): C₅₄H₇₄Cl₆N₄Pd₂
• CAS Number: 2417402-64-1
• Molecular Weight: 1204.75
• UNSPSC Code: 12352100
• PubChem Substance ID: 32347246

Properties

• Quality Level: 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]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.

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.

Safety Information

• Pictograms: GHS05,GHS07,GHS09
• Signal Word: Danger
• Hazard Statements: H302,H318,H410
• Precautionary Statements: 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 Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable