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Safety Information

660272

Sigma-Aldrich

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

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About This Item

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

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

Related Categories

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H317,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

660272-VAR:
660272-1G:
660272-BULK:
660272-250MG:

Certificates of Analysis (COA)

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Catalysts for Cross-Coupling Reactions with Non-activated Alkyl Halides.
Frisch AC and Beller M.
Angewandte Chemie (International Edition in English), 44(5), 674-688 (2005)

Articles

NHC-based Palladium Catalysts

In collaboration with Umicore AG and Co.,1 we are pleased to offer a series of robust Pd(II) and Pd(0) complexes employed as the linchpin in C–C bond forming reactions.

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