palladium(2+) ion bis(benzonitrile) dichloride

• ChemBase编号: 302706
• 分子式: C14H10Cl2N2Pd
• 平均质量: 383.5686
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: palladium(2+) ion bis(benzonitrile) dichloride
• IUPAC传统名: palladium(2+) ion bis(benzonitrile) dichloride
• 别名: 反式双(苄腈)二氯钯(II); Dichlorobis(benzonitrile)palladium(II); trans-Bis(benzonitrile)dichloropalladium(II)

登记号

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

理论计算性质

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 1.829342
• LogD (pH = 7.4): 1.829342
• Log P: 1.829342
• 摩尔折射率: 31.7796 cm^3
• 极化性: 12.177798 Å^3
• 极化表面积: 23.79 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Soluble in acetone, chloroform
• 外观: Powder

安全信息

• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: UN3439
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): III
• 危险公开号: 23/24/25
• 安全公开号: 4-9-20-27-36/37-45
• TSCA收录: 否
• GHS危险品标识: GHS06
• GHS危险声明: H301-H311-H331
• GHS警示性声明: P261-P301+P310-P361-P302+P352-P405-P501A

产品相关信息

• 纯度: Pd 27.1%

参考文献

• 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.