palladium(2+) ion bis(benzonitrile) dichloride

• ChemBase ID: 302706
• Molecular Formular: C14H10Cl2N2Pd
• Molecular Mass: 383.5686
• Monoisotopic Mass: 381.92558969
• SMILES: c1ccc(cc1)C#N.c1ccc(cc1)C#N.[Cl-].[Cl-].[Pd+2]
• Canonical SMILES: N#Cc1ccccc1.N#Cc1ccccc1.[Cl-].[Cl-].[Pd+2]
• InChI: InChI=1S/2C7H5N.2ClH.Pd/c2*8-6-7-4-2-1-3-5-7;;;/h2*1-5H;2*1H;/q;;;;+2/p-2
• InChIKey: WXNOJTUTEXAZLD-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: palladium(2+) ion bis(benzonitrile) dichloride
• IUPAC Traditional name: palladium(2+) ion bis(benzonitrile) dichloride
• Synonyms: Dichlorobis(benzonitrile)palladium(II); trans-Bis(benzonitrile)dichloropalladium(II); 反式双(苄腈)二氯钯(II)

Database IDs

• CAS Number: 14220-64-5
• EC Number: 238-085-3
• MDL Number: MFCD00013123

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.829342
• LogD (pH = 7.4): 1.829342
• Log P: 1.829342
• Molar Refractivity: 31.7796 cm^3
• Polarizability: 12.177798 Å^3
• Polar Surface Area: 23.79 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Soluble in acetone, chloroform
• Apperance: Powder

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: UN3439
• Hazard Class: 6.1
• Packing Group: III
• Risk Statements: 23/24/25
• Safety Statements: 4-9-20-27-36/37-45
• TSCA Listed: 否
• GHS Pictograms: GHS06
• GHS Hazard statements: H301-H311-H331
• GHS Precautionary statements: P261-P301+P310-P361-P302+P352-P405-P501A

Product Information

• Purity: Pd 27.1%

REFERENCES

• Air-stable, organic-soluble Pd complex, which catalyzes a variety of reactions:
• Trimerization of alkynes to aromatic compounds: J. Am. Chem. Soc., 84, 2329 (1962); Synthesis, 659 (1986). Review: Acc. Chem. Res., 9, 93 (1976). Cyclopropanation of various allylic alcohols, ethers and amines by diazomethane: Synthesis, 246 (1990). In the presence of a tert-amine, catalyzes the cyclization of 3- and 4-alkynoic acids to unsaturated lactones in high yield: Tetrahedron Lett., 25, 5323 (1984):
  
• Catalyst for the Ag₂O promoted Suzuki coupling of arylboronic acids with sensitive halides: Org. Synth., 75, 69 (1997); for reaction scheme, see 4-Methoxybenzeneboronic acid, A14462.
• In combination with N,N-dimethylglycine, forms a highly active phosphine-free catalyst system for the Heck reaction of aryl bromides: Tetrahedron Lett., 39, 8449 (1998).
• In combination with CuI, terminal alkynes couple with vinyl chlorides to give conjugated enynes in high yield: Tetrahedron Lett., 32, 6109 (1991). This has been exploited in a synthesis of lipoxin B₄: Synlett, 217 (1993), and of (Z)- and (E)-enediynes from the isomeric 1,2-dichloroethylenes: Tetrahedron Lett., 35, 3543 (1994).
• In combination with Ti(O-i-Pr)₄, promotes the symmetrical coupling of arylsulfonyl chlorides to biaryls: Chem. Lett., 459 (1990).
• For a brief feature on uses in synthesis, see: Synlett, 1449 (2006). See also Bis(acetonitrile)dichloropalladium(II), 10002.