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668923

Sigma-Aldrich

Di-μ-chlorobis[5-chloro-2-[(4-chlorophenyl)(hydroxyimino-κN)methyl]phenyl-κC]palladium dimer

97%

Synonym(s):

Nájera Catalyst I, Di-chlorobis[5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl-C]di-palladium

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About This Item

Empirical Formula (Hill Notation):
C26H16Cl6N2O2Pd2
CAS Number:
287410-78-0
Molecular Weight:
813.98
UNSPSC Code:
12161600
PubChem Substance ID:
24885009
NACRES:
NA.22

Assay

97%

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

SMILES string

O\N=C(/c1ccc(Cl)cc1)c2ccc(Cl)cc2[Pd]Cl.O\N=C(/c3ccc(Cl)cc3)c4ccc(Cl)cc4[Pd]Cl

InChI

1S/2C13H8Cl2NO.2ClH.2Pd/c2*14-11-5-1-9(2-6-11)13(16-17)10-3-7-12(15)8-4-10;;;;/h2*1-3,5-8,17H;2*1H;;/q;;;;2*+1/p-2/b2*16-13+;;;;

InChI key

GIMFEGPTUHULMU-VAABLSLRSA-L

Application

Catalyst for:
  • Suzuki coupling
  • Suzuki-Miyaura coupling
  • Najera palladacycle-catalyzed intermolecular Heck reaction of Morita-Baylis-Hillman adducts
  • Hiyama cross-coupling
  • Palladium-catalyzed acylation of terminal alkynes with acid chlorides
  • Copper and amine free Sonogashira coupling reaction
Highly effective catalyst for multiple aryl vinylation via Heck coupling. Palladacycle catalyst employed in a variety of carbon-carbon bond forming reactions.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

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 Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBN4383V
MKBG2345V
12523EE

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Synthesis, 1713-1713 (2004)
European Journal of Organic Chemistry, 3482-3482 (2005)

Articles

Palladacycle Coupling Catalysts

Palladacyclic catalysts by Bedford's group facilitate coupling reactions with low catalyst loadings and challenging aryl chlorides.

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