Allylpalladium(II) chloride dimer - ≥99.95% metals basis , CAS No.12012-95-2

CAS: 12012-95-2 Cat. No.: A284049 Molecular Weight: 365.89 Beilstein Registry Number: 4124623 EC Number: 234-579-8 PubChem CID: 61538

GRADE & PURITY ≥99.95% metals basis

Synonyms

[Pd(allyl)Cl]2 | Bis((eta3-allyl)(chloro)palladium) | Bis((mu-chloro)(2-propenyl)palladium) | Bis(allyl(mu-chloro)palladium) | Bis(eta3-allyl)dichlorodipalladium | Palladium allyl chloride dimer | MFCD00044874 | Di-mu-chloro-bis(eta-allyl)palladium | Q101

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

Overview

Allylpalladium(II) chloride dimer is employed as catalyst in Heck reaction. It also participates as catalyst in the tandem nucleophilic allylation-alkoxyallylation reaction of the alkynylaldehydes with allyl chloride and allyltributylstannane.
Allylpalladium(II) chloride dimer has been employed for the following studies:
● Synthesis of cationic palladium cataysts, used in the microwave-assisted Heck arylation.
● Synthesis of N-heterocyclic carbene-palladium-η3-allyl chloride complexes, which are efficient catalyst for the Suzuki-Miyaura cross-coupling of aryl bromides and activated aryl chlorides.
● Synthesis of 1,4-diallyl-1,2-dihydroisoquinolines.
● As catalyst for greener Buchwald-Hartwig coupling in TPGS-750-M.

Application

Precatalysts for Asymmetric and Cross-Coupling Catalysis

Product class
M-C, Homogeneous Catalysts, Allyl Ligands

Reaction type
Cross Coupling Reactions with Arenes, Amination, Allylic Alkylation, Buchwald-Hartwig Aminaton, Asymmetric Reactions, CH-Activation, Mizoroki Heck Coupling Reaction

Chemical properties

Chemical formula

C6H10Cl2Pd2

Empirical formula

[Pd(allyl)Cl]2

Molecular weight

365.89

Metal

Pd

Theoretical metal content

58

Physical state

crystalline

Color

yellow

Metal purity

99.95

Specifications

Synonyms

[Pd(allyl)Cl]2 | Bis((eta3-allyl)(chloro)palladium) | Bis((mu-chloro)(2-propenyl)palladium) | Bis(allyl(mu-chloro)palladium) | Bis(eta3-allyl)dichlorodipalladium | Palladium allyl chloride dimer | MFCD00044874 | Di-mu-chloro-bis(eta-allyl)palladium | Q101

Specifications & Purity

≥99.95% metals basis

Legal Information

Product of Umicore

Storage

Store at 2-8°C, Protected from light, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99.95% metals basis

Names and Identifiers

• Canonical Smiles: [CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]
• IUPAC Name: chloropalladium(1+);prop-1-ene
• InChIKey: PENAXHPKEVTBLF-UHFFFAOYSA-L
• INCHI: 1S/2C3H5.2ClH.2Pd/c2*1-3-2;;;;/h2*3H,1-2H2;2*1H;;/q2*-1;;;2*+2/p-2
• Isomeric SMILES: [CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]
• WGK Germany: 3
• RTECS: RT3510000
• PubChem CID: 61538
• Molecular Weight: 365.89
• Beilstein: 4124623

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic salts
    • Class Organic metal salts
      • Subclass Organic metal halides

• Kingdom: Organic compounds
• Superclass: Organic salts
• Class: Organic metal salts
• Subclass: Organic metal halides
• Intermediate Tree Nodes: Not available
• Direct Parent: Organic metal halides
• Alternative Parents: Organic transition metal salts Unsaturated aliphatic hydrocarbons Olefins Hydrocarbon derivatives
• Molecular Framework: Not available
• Substituents: Organic metal halide - Organic transition metal salt - Unsaturated aliphatic hydrocarbon - Unsaturated hydrocarbon - Hydrocarbon derivative - Olefin - Hydrocarbon - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as organic metal halides. These are organic compounds containing metals and halogens. Some are ionic while others are covalently bonded.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Very soluble in dichloromethane and dichloroethane. Slightly soluble in toluene, insoluble in waterSoluble in chloroform, benzene, acetone and dichloromethane, dichloroethane and methanol. Slightly soluble in toluene. Insoluble in water.
• Sensitivity: Light & air & moisture sensitive
• Melt Point(°C): 120°C
• Molecular Weight: 365.900 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 365.823 Da
• Monoisotopic Mass: 363.823 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 14.400
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 4

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