bis(chloro({5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl})palladium)

• ChemBase ID: 152882
• Molecular Formular: C26H16Cl6N2O2Pd2
• Molecular Mass: 813.97544
• Monoisotopic Mass: 809.74126584
• SMILES: c1c(ccc(c1)Cl)/C(=N/O)/c1c(cc(cc1)Cl)[Pd]Cl.c1c(ccc(c1)Cl)/C(=N/O)/c1c(cc(cc1)Cl)[Pd]Cl
• Canonical SMILES: Cl[Pd]c1cc(Cl)ccc1/C(=N\O)/c1ccc(cc1)Cl.Cl[Pd]c1cc(Cl)ccc1/C(=N\O)/c1ccc(cc1)Cl
• InChI: 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
• InChIKey: GIMFEGPTUHULMU-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(chloro({5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl})palladium)
• IUPAC Traditional name: bis(chloro({5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl})palladium)
• Synonyms: Di-chlorobis[5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl-C]di-palladium; Nájera Catalyst I; Di-μ-chlorobis[5-chloro-2-[(4-chlorophenyl)(hydroxyimino-κN)methyl]phenyl-κC]palladium dimer; Nájera 催化剂 I; 二-氯双[5-氯-2-[(4-氯苯基)(羟基亚氨基)甲基]苯基-C]二钯; 二-μ-氯双[5-氯-2-[(4-氯苯基)(羟基亚氨基-κN)甲基]苯基-κC]钯二聚物

Database IDs

• CAS Number: 287410-78-0
• PubChem SID: 162247025; 24885009
• PubChem CID: 71311574

CALCULATED PROPERTIES

• Acid pKa: 7.7021036
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.4526544
• LogD (pH = 7.4): 4.2808285
• Log P: 4.4554
• Molar Refractivity: 75.6174 cm^3
• Polarizability: 33.345844 Å^3
• Polar Surface Area: 32.59 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C26H16Cl6N2O2Pd2

DETAILS

Sigma Aldrich - 668923

Packaging
1 g in glass bottle
250 mg in glass bottle
Application
Catalyst for:
• Suzuki coupling1
• Suzuki-Miyaura coupling2
• Najera palladacycle-catalyzed intermolecular Heck reaction of Morita-Baylis-Hillman adducts3
• Hiyama cross-coupling4
• Palladium-catalyzed acylation of terminal alkynes with acid chlorides5
• Copper and amine free Sonogashira coupling reaction6
Highly effective catalyst for multiple aryl vinylation via Heck coupling. Palladacycle catalyst employed in a variety of carbon-carbon bond forming reactions.