tripalladium(2+) ion hexaacetate

• ChemBase ID: 302722
• Molecular Formular: C12H18O12Pd3
• Molecular Mass: 673.52412
• Monoisotopic Mass: 671.79028402
• SMILES: CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].CC(=O)[O-].[Pd+2].[Pd+2].[Pd+2]
• Canonical SMILES: [O-]C(=O)C.[O-]C(=O)C.[O-]C(=O)C.[O-]C(=O)C.[O-]C(=O)C.[O-]C(=O)C.[Pd+2].[Pd+2].[Pd+2]
• InChI: InChI=1S/6C2H4O2.3Pd/c6*1-2(3)4;;;/h6*1H3,(H,3,4);;;/q;;;;;;3*+2/p-6
• InChIKey: VFXXDLSJPITVGX-UHFFFAOYSA-H

NAMES AND DATABASE IDS

Names

• IUPAC name: tripalladium(2+) ion hexaacetate
• IUPAC Traditional name: tripalladium(2+) ion hexaacetate
• Synonyms: Palladium diacetate; Palladium(II) acetate, trimer; Acetic acid palladium(II) salt; 乙酸钯(II), 三聚体

Database IDs

• CAS Number: 3375-31-3
• EC Number: 222-164-4
• MDL Number: MFCD00012453
• Merck Index: 146991

CALCULATED PROPERTIES

• Acid pKa: 4.54344
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -1.2242727
• LogD (pH = 7.4): -2.9968748
• Log P: -0.22334571
• Molar Refractivity: 23.4808 cm^3
• Polarizability: 4.912116 Å^3
• Polar Surface Area: 40.13 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Soluble as monomer in glacial acetic acid or as trimer in benzene
• Apperance: Needles; Powder
• Melting Point: ca 205°C dec.

Safety Information

• RTECS: AJ9000000
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 41-43-53
• Safety Statements: 24-26-37/39-60-61
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07
• GHS Hazard statements: H318-H317-H413
• GHS Precautionary statements: P261-P280-P305+P351+P338-P302+P352-P321-P501A

Product Information

• Purity: 99.98% (metals basis), Pd 47% min; Pd 45.9-48.4%

REFERENCES

• o-Allylic or o-vinylic phenols undergo phosphine-free Pd-catalyzed cross-coupling with vinylic halides and triflates, giving dihydrobenzopyrans and dihydrobenzofurans respectively: Tetrahedron Lett., 39, 237 (1998):
  
• In the presence of TBAB, catalyzes direct homocoupling of aryl halides: Tetrahedron Lett., 39, 2559 (1998).
• Use in an improved "Wacker" oxidation of terminal alkenes to 2-alkanones, with p-Benzoquinone, A13162, as the co-oxidant, gives rates up to 50 times higher than earlier procedures: J. Org. Chem., 55, 2924 (1990).
• Also catalyzes the allylic acetoxylation of cycloalkenes: Org. Synth. Coll., 8, 137 (1993).
• For catalysis of the efficient "ligandless" Suzuki cross-coupling of arylboronic acids with aryl iodides, see: J. Org. Chem., 59, 5034 (1994); Org. Synth., 75, 61 (1997).
• For a brief feature on uses of palladium acetate in synthesis, see: Synlett, 329 (2006).
• For the Heck-type reaction of arenediazonium salts with alkenes, see p-Anisidine, A10946.
• Widely used as catalyst, in the presence of a phosphine ligand and a base, in the Heck (or Mizoroki-Heck) reaction, for coupling of aryl or vinyl halides with alkenes. Reviews: Org. React., 27, 345 (1982); Acc. Chem. Res., 12, 146 (1979); 28, 2 (1995);Angew. Chem. Int. Ed., 33, 2379 (1994); Chem. Rev., 100, 3009 (2000). In many reactions, e.g. the arylation of ɑ?-unsaturated esters, Tri(o-tolyl)phosphine, A12093 is superior to triphenylphosphine: J. Org. Chem., 43, 2952 (1978).