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660361

Sigma-Aldrich

CX21

Umicore, 98%

Synonym(s):

Allyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloropalladium(II), (NHC)Pd(allyl)Cl, Allylchloro[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]palladium(II)

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About This Item

Empirical Formula (Hill Notation):
C30H41N2ClPd
CAS Number:
478980-03-9
Molecular Weight:
571.53
MDL number:
MFCD08561131
UNSPSC Code:
12161600
PubChem Substance ID:
24884472
NACRES:
NA.22

Quality Level

100

Assay

98%

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

[CH2][CH][CH2].CC(C)c1cccc(C(C)C)c1N2C=CN(C2[Pd]Cl)c3c(cccc3C(C)C)C(C)C

InChI

1S/C27H37N2.C3H5.ClH.Pd/c1-18(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;1-3-2;;/h9-21H,1-8H3;3H,1-2H2;1H;/q;;;+1/p-1

InChI key

YVIDBHQABBIAAW-UHFFFAOYSA-M

Related Categories

General description

Allyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloropalladium(II) is an air-stable, well-defined palladium N-heterocyclic carbene complex, which can efficiently catalyze α-arylation of ketones.

Application

Catalyst for the arylation of ketones, Suzuki coupling reaction, Buchwald-Hartwig amination reaction, dehalogenation of aryl chlorides, and oxidation of secondary alcohols.

Legal Information

Product of Umicore

Additional information available at www.pmc.umicore.com

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - 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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR1169
MKCV3999
MKCP1718
MKCL4559
MKCL1752

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Well-defined, air-stable (NHC) Pd (Allyl) Cl (NHC= N-heterocyclic carbene) catalysts for the arylation of ketones.
Viciu MS, et al.
Organic Letters, 4(23), 4053-4056 (2002)

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