(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium (HCID 6505921)

Names & identifiers

Preferred name: (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium
IUPAC: bis((1E,4E)-1,5-diphenylpenta-1,4-dien-3-one);palladium
English name: Tris(dibenzylideneacetone)dipalladium
Molecular formula: C51H42O3Pd2
Molecular weight: 915.71738

Names & synonyms

52409-22-0(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; PalladiumRefChem:392699620-687-632005-36-0Bis(dibenzylideneacetone)palladium(0)PD(DBA)2MFCD00051942(1E,4E)-Bis(dibenzylideneacetone)palladiumC34H28O2Pd190385-99-0Bis(dibenzylideneacetone)palladium (Technical Grade)

Show more names

Pd(dba)3PALLADIUM(0) BIS(DIBENZYLIDENEACETONE)Bis(dibenzylideneacetone)dipalladiumTris(dibenzylideneacetone)diplalladium(I)tris(dibenzylideneacetone)dipalladium(o)(pd2(dba)3)Tris(dibenzylideneacetoneTris(dibenzylideneacetone)dipalladiumBIS(DIBENZYLIDENEACETONE) PALLADIUM(0)Tris(dibenzilideneacetone)dipalladium(0)

60748-47-2TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(O)SCHEMBL2438441bis(dibenzylideneactone)palladiumbis (dibenzylideneacetone)palladiumbis(dibenzylidene acetone)palladiumbis(dibenzylidene-acetone)palladiumbis(dibenzylideneacetone)-palladium

Database identifiers

CAS: 52409-22-0
PubChem CID: 6505921
EC Number: 620-687-6

Properties

Computed structural properties

Topological polar surface area: 34.1 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 8
Heavy atoms: 37
Formal charge: 0
Complexity: 272

Physicochemical properties

Melting point: 152 · 152-155 °C(lit.)
storage temp.: 2 · Keep in dark place,Inert atmosphere,2-8°C
InChI: InChI=1S/2C17H14O.Pd/c2*18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;/h2*1-14H;/b2*13-11+,14-12+;
InChIKey: UKSZBOKPHAQOMP-SVLSSHOZSA-N
SMILES: [Pd].C(=C/C1=CC=CC=C1)\C(/C=C/C1=CC=CC=C1)=O.C(=C/C1=CC=CC=C1)\C(/C=C/C1=CC=CC=C1)=O
CAS DataBase Reference: 52409 · 52409-22-0(CAS DataBase Reference)
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H332
Precautionary statements: 261 · P261-P271-P304+P340-P312-P264-P270-P301+P312-P330-P501
Hazard Codes: Xi
Risk Statements: 36 · 36/38
Safety Statements: 22 · 22-24/25
WGK Germany: 3 · 3

Safety & regulation

GHS classification

GHS Classification · 5 items

Danger

H228 (50%): Flammable solid [Danger Flammable solids]；H302 (75%): Harmful if swallowed [Warning Acute toxicity, oral]；H312 (25%): Harmful in contact with skin [Warning Acute toxicity, dermal]；H315 (25%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (25%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H332 (75%): Harmful if inhaled [Warning Acute toxicity, inhalation]

P210, P240, P241, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 4 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesFlam. Sol. 1 (50%)；Acute Tox. 4 (75%)；Acute Tox. 4 (25%)；Skin Irrit. 2 (25%)；Eye Irrit. 2 (25%)；Acute Tox. 4 (75%)

Toxicology

Health EffectsContact with palladium may cause palladium sensitivity and allergy. Animal studies have shown that palladium may damage the liver and kidney. (L798)

Toxicity Summary · 1 item

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)

Signs and SymptomsSkin contact with palladium may cause contact dermatitis, erythema, and oedema. (L798)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

wgk: 3
risk_code: 36/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 22-24/25
Hazard statements: H302-H332
Precautionary statements: P261-P271-P304+P340-P312-P264-P270-P301+P312-P330-P501

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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)

Applications · 1 item

UsesTris(dibenzylideneacetone)dipalladium is used as a source of soluble Pd(0), in particular as a catalyst for various coupling reactions. Examples of reactions using this reagent are the Negishi coupling, Suzuki coupling, Carroll rearrangement, and Trost asymmetric allylic alkylation, as well as Buchwald–Hartwig amination