trans-Bis(benzonitrile)dichloropalladium(II)

• Catalog No.: 10006
• CAS Number: 14220-64-5
• M. F.: C14H10Cl2N2Pd
• M. W.: 383.5686
• Purity: Pd 27.1%

SYNONYMS

• Title: 反式双(苄腈)二氯钯(II)
• IUPAC name: palladium(2+) ion bis(benzonitrile) dichloride
• IUPAC Traditional name: palladium(2+) ion bis(benzonitrile) dichloride
• Synonyms: Dichlorobis(benzonitrile)palladium(II)

DATABASE IDS

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

PROPERTIES

• Purity: Pd 27.1%
• Apperance: Powder
• Solubility: Soluble in acetone, chloroform
• GHS Hazard statements: H301-H311-H331
• European Hazard Symbols: Toxic (T)
• GHS Precautionary statements: P261-P301+P310-P361-P302+P352-P405-P501A
• Risk Statements: 23/24/25
• Safety Statements: 4-9-20-27-36/37-45
• TSCA Listed: 否
• Hazard Class: 6.1
• UN Number: UN3439
• Packing Group: III

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.