| Identification | More | [Name]
Palladium diacetate | [CAS]
3375-31-3 | [Synonyms]
ACETIC ACID PALLADIUM(II) SALT
PALLADIUM(+2)ACETATE
PALLADIUM ACETATE
PALLADIUM DIACETATE
PALLADIUM(II) ACETATE
PALLADIUM(II) ACETATE IN IONIC LIQUID ON SILICA
PALLADIUM (II) ACETATE, TRIMER
PALLADIUM II ACETATE TRIMERIC ORANGE-BROWN
PD(OAC)2 (TRIMER) SALT
Aceticacid,palladium(2+)salt
aceticacid,palladium(2++)salt
aceticacidpalladiumsalt
bis(acetato)palladium
bisacetylpalladium
diacetatopalladium
diacetoxypalladium
palladousacetate
hexakis(acetato)tripalladium
Palladium(II)acetat
Palladiumacetatemingoldbrownxtl | [EINECS(EC#)]
222-164-4 | [Molecular Formula]
C4H6O4Pd | [MDL Number]
MFCD00012453 | [Molecular Weight]
224.51 | [MOL File]
3375-31-3.mol |
| Chemical Properties | Back Directory | [Appearance]
brown needles | [Melting point ]
205 °C
| [vapor pressure ]
0.002Pa at 25℃ | [storage temp. ]
Store at R.T. | [solubility ]
Soluble as monomer in glacial acetic acid or as trimer in benzene. | [form ]
Various Forms In Red-(Powder/Flake/Crystalline/Beads) | [color ]
Red-brown | [PH]
2-3 (H2O, 20℃)(aqueous suspension) | [PH Range]
2.0 - 3.0 at 20 °C | [Water Solubility ]
insoluble | [Hydrolytic Sensitivity]
4: no reaction with water under neutral conditions | [Sensitive ]
Hygroscopic | [λmax]
400nm(EtOH)(lit.) | [Detection Methods]
T | [Merck ]
14,6991 | [BRN ]
6086766 | [InChIKey]
PCUVQHHZCJMCHO-UHFFFAOYSA-M | [LogP]
-0.17 at 20℃ | [CAS DataBase Reference]
3375-31-3(CAS DataBase Reference) | [Storage Precautions]
Store under nitrogen;Air sensitive | [EPA Substance Registry System]
3375-31-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R41:Risk of serious damage to eyes.
R36/37/38:Irritating to eyes, respiratory system and skin .
R40:Limited evidence of a carcinogenic effect. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S39:Wear eye/face protection .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
3261 | [WGK Germany ]
2
| [RTECS ]
AJ1900000
| [F ]
10-23 | [TSCA ]
Yes | [HS Code ]
28439090 | [Toxicity]
LD50 orally in Rabbit: >= 5110 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Acetic acid-->Hydrazine hydrate-->Palladium chloride-->Sodium formate | [Preparation Products]
(S)-(-)-7,7'-BIS[DI(3,5-DIMETHYLPHENYL)PHOSPHINO]-2,2',3,3'-TETRAHYDRO-1,1'-SPIROBIINDANE-->(R)-7,7'-BIS(DIPHENYLPHOSPHINO)-1,1'-SPIROBIINDANE-->Bergapten-->(R)-(+)-7,7'-BIS(DIPHENYLPHOSPHINO)-2,2',3,3'-TETRAHYDRO-1,1'-SPIROBIINDANE-->(R)-(+)-7,7'-BIS[DI(4-METHYLPHENYL)PHOSPHINO]-2,2',3,3'-TETRAHYDRO-1,1'-SPIROBIINDANE-->(S)-7,7'-Bis[di(p-methylphenyl)phosphino]-1,1'-spirobiindane ,97%-->4-(2-KETO-1-BENZIMIDAZOLINYL)PIPERIDINE-->Diphenylacetylene-->C-(3,4-DIHYDRO-2H-BENZO[1,4]OXAZIN-3-YL)-METHYLAMINE-->Ethyl (R)-2-hydroxy-4-phenylbutyrate-->3-AMINOBIPHENYL-->2,3-DIHYDRO-1H-INDOLE-5-CARBOXYLIC ACID-->5-CYANO-2,3-DIHYDRO-1H-INDOLE-->INDOLINE-6-CARBOXYLIC ACID-->ethyl indoline-6-carboxylate-->3-PHENYLBENZYLAMINE-->1-(4-Pyridyl)piperazine-->4,6-Diamino-2-pyrimidinol-->2-MORPHOLINO-5-(TRIFLUOROMETHYL)BENZALDEHYDE-->ethyl 1H-indole-6-carboxylate-->4-Aminobiphenyl-->N,N'-Bis- (1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine-->1-ACETYL-5-AMINO-2,3-DIHYDRO-(1H)-INDOLE-->5-Phenylthiophene-2-carboxylic acid-->5-PHENYL-2-THIOPHENECARBALDEHYDE-->(E)-METHYL 3-(4-BROMOPHENYL)ACRYLATE-->4-Aminophenylboronic acid pinacol ester-->5-Methylindole-->3-Phenyl-1H-pyrazole-->Allyl acetate |
| Hazard Information | Back Directory | [Chemical Properties]
brown needles | [Uses]
Palladium (II) Acetate Trimer is used in Suzuki-Miyaura cross-coupling reactions and a catalyst for intramolecular coupling. It also serves to catalyze the chemoselective reduction of nitroarenes. | [Definition]
Palladium acetate is a chemical compound of palladium. It is used as a catalyst for many organic reactions and as a precursor to other palladium(II) compounds. 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. (Toxin and Toxin Target Database (T3DB)) | [Preparation]
The synthesis of palladium acetate was first reported by Wilkinson et al.,where glacial acetic acid containing palladium powder is heated at reflux with a minimal amount of nitric acid until the generation of brown NOx fumes ceases. Although this is a relatively old method, it is still the most commercially employed route for the synthesis of palladium acetate, considering the process economics. Palladium (II) Acetate can be synthesized in two steps from palladium sponge via the intermediate dinitrate by first combining it with hot glacial acetic acid and nitric acid:
Pd + 2 HNO3 → Pd(NO3)2 + H2
Pd(NO3)2 + 2 CH3COOH → Pd(O2CCH3)2 + 2 HNO3 | [Reactions]
-
Efficient catalyst for the arylation of olefins (Heck reaction).
-
Catalyst for cross-coupling reactions.
-
Catalyst for C-H activation.
-
Precatalyst for enantioselective decarboxylative protonation of allyl β-ketoesters.
| [General Description]
Palladium(II) acetate(3375-31-3) is a homogenous oxidation catalyst. It participates in the activation of alkenic and aromatic compounds towards oxidative inter- and intramolecular nucleophilic reactions. Crystals of palladium(II) acetate have a trimeric structure, having symmetry D3h. Each of the palladium atoms in the crystals are joined to the other two by double acetate bridges. Microencapsulation of palladium(II) acetate in polyurea affords polyurea-encapsulated palladium(II) acetate. It is a versatile heterogeneous catalyst for various phosphine-free cross-coupling reactions. It participates as catalyst in the Heck coupling reaction of pthalides with different alkenes.
| [Flammability and Explosibility]
Nonflammable | [Safety Profile]
Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of palladium. | [Purification Methods]
It recrystallises from CHCl3 as purple crystals. It can be washed with AcOH and H2O and dried in air. Large crystals are obtained by dissolving it in *C6H6, adding half its volume of AcOH and allowing it to evaporate slowly at room temperature. It forms green adducts with nitrogen donors, it dissolves in KI solution to form solid PdI2 and a red solution of PdI42-, but is insoluble in aqueous saturated NaCl, and NaOAc. It dissolves in HCl to form PdCl42-. It is soluble in CHCl3, CH2Cl2, Me2CO, MeCN, Et2O, but it is insoluble in H2O, and decomposes when warmed in alcohols in which it is also insoluble. [Morehouse et al. Chem Ind (London) 544 1964, Stephenson et al. J Chem Soc 3632 1965, Skapski & Smart J Chem Soc (D) 658 1970, Heck Acc Chem Res 12 146 1979.] |
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