HuagongsheHuagongshe Chemistry Print Report · For research reference only
(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium
PD(DBA)2 · Pd(dba)3 · PALLADIUM(0) BIS(DIBENZYLIDENEACETONE) · Bis(dibenzylideneacetone)dipalladium · Tris(dibenzylideneacetone)diplalladium(I) · tris(dibenzylideneacetone)dipalladium(o)(pd2(dba)3) · Tris(dibenzylideneacetone · Tris(dibenzylideneacetone)dipalladium
Identifiers & Physical Properties
| CAS No. | 52409-22-0 |
|---|---|
| Molecular formula | C34H28O2Pd |
| Average molar mass | 575 g/mol |
| Monoisotopic mass | 574.11241 g/mol |
| SMILES | O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd] |
| InChIKey | UKSZBOKPHAQOMP-SVLSSHOZSA-N |
| PubChem CID | 6505921 |
| EC No. | 620-687-6 |
Chemical & Physical Properties
| Topological polar surface area | 34.1 |
|---|---|
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 8 |
| Heavy atoms | 37 |
| Formal charge | 0 |
| Complexity | 272 |
| Melting point | 152-155 °C(lit.) |
| Storage conditions | 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 | 52409-22-0(CAS DataBase Reference) |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302-H332 |
| GHS precautionary statements | P261-P271-P304+P340-P312-P264-P270-P301+P312-P330-P501 |
| Hazard symbols | Xi |
| Risk statements (R) | 36/38 |
| Safety statements (S) | 22-24/25 |
| Water hazard class (WGK) | 3 |
Safety & Regulations
| GHS classification | DangerH228 (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 Classes and Categories | Flam. Sol. 1 (50%)Acute Tox. 4 (75%)Acute Tox. 4 (25%)Skin Irrit. 2 (25%)Eye Irrit. 2 (25%) |
| Health effects | Contact with palladium may cause palladium sensitivity and allergy. Animal studies have shown that palladium may damage the liver and kidney. (L798) |
| 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) |
| Signs and Symptoms | Skin contact with palladium may cause contact dermatitis, erythema, and oedema. (L798) |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Water hazard class (WGK) | 3 |
| Risk statements (R) | 36/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| Safety statements (S) | 22-24/25 |
| GHS hazard statements | H302-H332 |
| GHS precautionary statements | P261-P271-P304+P340-P312-P264-P270-P301+P312-P330-P501 |
Applications & Uses
Uses
Tris(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