Basic information
- CAS
12012-95-2- Standard SMILES
C=C[CH2-].C=C[CH2-].[Cl][Pd+].[Cl][Pd+]- InChIKey
PENAXHPKEVTBLF-UHFFFAOYSA-L- Molecular formula
- C6H10Cl2Pd2
- Average molar mass
- 365.9 g/mol
Overview
Allyl palladium(II) chloride dimer is a organopalladium compound. It is an important catalyst used in organic synthesis. Palladium is a chemical element with the chemical symbol Pd and an atomic number of 46. It is found as a free metal alloyed with gold and other platinum group metals and in the rare minerals cooperite and polarite. (L794, A27)
Names & identifiers
- Preferred name
- Palladium, di-mu-chlorobis(eta3-2-propenyl)di-
- IUPAC
- bis(chloropalladium(1+));bis(prop-1-ene)
- English name
- Allylpalladium(II) Chloride Dimer
- Molecular formula
- C6H10Cl2Pd2
- Molecular weight
- 365.89
Names & synonyms
Palladium, di-mu-chlorobis(eta3-2-propenyl)di-RefChem:858349Palladium, di-.mu.-chlorobis(.eta.3-2-propenyl)di-Palladium, di-mu-chlorobis(eta3-2-propenyl)di-(9CI)Allyl palladium (II) chloride dimer12012-95-2Allylpalladium chloride dimerAllylpalladium(II) chloride dimerallylpalladium(II) chloridePalladium allyl chloride dimer[Pd(allyl)Cl]2Bis(allyl(mu-chloro)palladium)
Show more names
[PdCl(C3H5)]2[PdCl(allyl)]2allylpaladiumAllylpalladium chlorideDi-μ-chlorobis(η3-2-propenyl)dipalladiumDiallyldichlorodipalladiumAllylpalladium(Ⅱ) chloride dimer
Bis(eta3-allyl)dichlorodipalladiumBis((eta3-allyl)(chloro)palladium)Bis((mu-chloro)(2-propenyl)palladium)Di-mu-chloro-bis(eta-allyl)palladiumbis(chloro(prop-2-en-1-yl)palladium)Bis(allyl)dichlorodipalladiumDiallydichlorodipalladiumpi-Allyl palladium chloride
Properties
Computed structural properties
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 14.4
Physicochemical properties
- Melting point
- 120 °C · 120°C (dec.)
- storage temp.
- 2 · 2-8°C
- form
- Crystals or Crystalline Powder
- color
- Yellow to green-yellow
- Water Solubility
- decomposes
- Sensitive
- Air Sensitive
- BRN
- 4124623 · 4124623
- InChI
- InChI=1S/2C3H2.2ClH.2Pd/c2*1-3-2;;;;/h2*1-2H;2*1H;;/q2*-1;;;2*+2/p-2
- InChIKey
- GSVMTGORPBRYQY-UHFFFAOYSA-L
- SMILES
- [Pd+2]123(C=C1[CH-]2)[Cl-][Pd+2]12(C=C1[CH-]2)[Cl-]3
- EWG's Food Scores
- 1 · 1
- NIST Chemistry Reference
- [Pd(Cl)(C3H5)]2(12012-95-2)
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315
Safety & regulation
GHS classification
GHS Classification
Danger
H228 (21.2%): Flammable solid [Danger Flammable solids]
P210, P240, P241, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 104 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Palladium, di-.mu.-chlorobis(.eta.3-2-propenyl)di-
Allyl palladium (II) chloride dimer: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Palladium, di-.mu.-chlorobis(.eta.3-2-propenyl)di-: Environment tier I assessment
Hazard Classes and CategoriesFlam. Sol. 1 (21.2%)
Toxicology
Health EffectsContact with palladium may cause palladium sensitivity and allergy. Animal studies have shown that palladium may damage the liver and kidney. (L798)
Exposure RoutesOral (A21) ; inhalation (A21) ; dermal (A21)
Toxicity Summary
Due to their ability to form strong complexes with both inorganic and organic ligands, palladium ions can disturb cellular equilibria, replace other essential ions, and interact with functional groups of macromolecules, such as proteins or DNA. Palladium complexes binding to DNA and RNA leads to strand breakage. Palladium ions are able to inhibit most major cellular functions, including DNA and RNA synthesis. Palladium compounds have been shown to bind to and inhibit various enzymes, including creatine kinase and prolyl hydroxylase. (L798)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Palladium may be absorbed through oral, dermal, and inhalation exposure. Once in the body it distributes to the kidney, liver, spleen, lymph nodes, adrenal gland, lung and bone. Palladium's ability to form complexes allows it the bind to amino acids, proteins, DNA, and other macromolecules. Palladium and its metabolites are excreted in the urine and faeces. (A21)
Uses & manufacturing
UsesAllylpalladium(II) chloride dimer is an important catalyst used in organic synthesis. (A27)
Applications
UsesAllylpalladium(II) chloride dimer is used as an important catalyst in Heck reaction. It reacts with cyclopentadienyl anion to give cyclopentadienyl allyl palladium. It acts as a precatalyst for asymmetric and cross-coupling catalysis. Further, it is used in the preparation of 1,4-diallyl-1,2-dihydroisoquinolines. It is also employed as a catalyst for greener Buchwald-Hartwig coupling reaction and involved in the synthesis of cationic palladium catalysts. In addition, it takes part in preparation of -heterocyclic carbene-palladium-eta3-allyl chloride complex, which is an efficient catalyst for the Suzuki-Miyaura cross-coupling reactions in synthetic chemistry.
Uses[Pd(allyl)Cl]2 can be used as a catalyst: For the silylation of organobromides. To synthesize α-aryl carbonyl compounds by coupling reaction between aldehydes and aryl halides. To prepare various arylthiophene derivatives by cross-coupling reaction with aryl halides via C-H functionalization. Application Guide for Palladium Catalyzed Cross-Coupling Reactions ChemDose: Convenient Dosing of Catalysts and Reagents
General DescriptionAllylpalladium(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.
Related reactions
2,033 records
Compound notes
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