660272

CX12

Umicore

• Synonym(s): 1,3-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (1,4-naphthoquinone)palladium(0) dimer, Bis[1,3-dihydro-1,3-(2,4,6-trimethylphenyl)-2H-imidazol-2-ylidene]bis[μ-[(2,3-η)-1,4-naphthalenedione-κO]]di-palladium, Naphthoquinone-1,3-bis(2,4,6-trimethylphenyl)-imidazole-2-ylidenepalladium(0), Pd(0)-naphthochinone-1,3-Bis(2,4,6-tri-methylphenyl)imidazol-2-ylidene
• Empirical Formula (Hill Notation): C₆₂H₆₀N₄O₄Pd₂
• CAS Number: 467220-49-1
• Molecular Weight: 1138.00
• MDL number: MFCD08705778
• UNSPSC Code: 12161600
• PubChem Substance ID: 24884468
• NACRES: NA.22

Properties

• description: Umicore
• form: solid
• reaction suitability: core: palladium; reaction type: Buchwald-Hartwig Cross Coupling Reaction; reaction type: Cross Couplings; reaction type: Heck Reaction; reaction type: Hiyama Coupling; reaction type: Negishi Coupling; reaction type: Sonogashira Coupling; reaction type: Stille Coupling; reaction type: Suzuki-Miyaura Coupling; reagent type: catalyst
• mp: >300 °C
• SMILES string: O=C1C=CC(=O)c2ccccc12.O=C3C=CC(=O)c4ccccc34.Cc5cc(C)c(N6C=CN(C6=[Pd])c7c(C)cc(C)cc7C)c(C)c5.Cc8cc(C)c(N9C=CN(C9=[Pd])c%10c(C)cc(C)cc%10C)c(C)c8
• InChI: 1S/2C21H24N2.2C10H6O2.2Pd/c2*1-14-9-16(3)20(17(4)10-14)22-7-8-23(13-22)21-18(5)11-15(2)12-19(21)6;2*11-9-5-6-10(12)8-4-2-1-3-7(8)9;;/h2*7-12H,1-6H3;2*1-6H;;
• InChI key: ZTBFODSKEBBIJJ-UHFFFAOYSA-N

Description

General description

1,3-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (1,4-naphthoquinone)palladium(0) dimer is an N-heterocyclic carbene based palladium catalyst that shows high catalytic activity in C-C coupling reactions.

Application

It can be used as a catalyst in the Kumada cross-coupling of aryl magnesium reagents with functionalized alkyl chlorides at room temperature to form substituted alkanes.

Other Notes

Product of Umicore

Additional information available at www.pmc.umicore.com

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H317,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves