palladium(2+) ion bis(triphenylphosphane) dichloride

• ChemBase编号: 126171
• 分子式: C36H30Cl2P2Pd
• 平均质量: 701.896922
• 单一同位素质量: 700.02346558
• SMILES: [Pd+2].[Cl-].[Cl-].c1c(P(c2ccccc2)c2ccccc2)cccc1.c1ccccc1P(c1ccccc1)c1ccccc1
• Canonical SMILES: c1ccc(cc1)P(c1ccccc1)c1ccccc1.c1ccc(cc1)P(c1ccccc1)c1ccccc1.[Cl-].[Cl-].[Pd+2]
• InChI: InChI=1S/2C18H15P.2ClH.Pd/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;;/h2*1-15H;2*1H;/q;;;;+2/p-2
• InChIKey: YNHIGQDRGKUECZ-UHFFFAOYSA-L

名称和登记号

名称

• IUPAC标准名: palladium(2+) ion bis(triphenylphosphane) dichloride
• IUPAC传统名: palladium(2+) ion bis(triphenylphosphine) dichloride
• 别名: 反式双(三苯基膦)二氯化钯(II); 反-双(三苯基膦)二氯化钯(II), Premion®; Bis(triphenylphosphine)palladium(II) dichloride; Bis(triphenylphosphine)dichloropalladium(II); trans-Dichlorobis(triphenylphosphine)palladium(II); trans-Dichlorobis(triphenylphosphine)palladium(II), Premion®

登记号

• CAS号: 13965-03-2
• EC号: 237-744-2
• MDL号: MFCD00009593
• PubChem SID: 162220512
• PubChem CID: 6102075; 84124
• Chemspider ID: 75895
• 维基百科标题: Bis(triphenylphosphine)palladium(II)_dichloride

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 5.1066
• LogD (pH = 7.4): 5.1066
• Log P: 5.1066
• 摩尔折射率: 81.6229 cm^3
• 极化性: 32.34495 Å^3
• 极化表面积: 0.0 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

分子性质

理化性质

• 外观: Crystalline; Powder
• 熔点: ca 310°C dec.

安全信息

• 保存注意事项: Hygroscopic
• RTECS编号: RT3578000
• 危险公开号: 53
• 安全公开号: 60-61
• TSCA收录: 否
• GHS危险声明: H413
• GHS警示性声明: P273-P501A

产品相关信息

• 纯度: 98%; 99.95% (metals basis), Pd 14.7% min; Pd 14.0% min

参考文献

• Catalyst for a wide range of coupling reactions:
• Terminal alkynes give a mixture of regioisomers.
• In combination with CuI and an amine, catalyzes the Sonogashira coupling of terminal alkynes with aryl, vinyl, styryl and 2-pyridyl halides: Tetrahedron Lett., 4467 (1975):
  
• An improved procedure uses triethylamine in THF with catalytic amounts of CuI and the complex, avoiding the need for excess of the acetylene, and gives good yields under mild conditions, even with unreactive aryl bromides: J. Org. Chem., 63, 8551 (1998).
• Catalyst for the Heck reaction (see Palladium(II) acetate, 10516). For effect of high pressure in accelerating the reaction, see: Tetrahedron Lett., 36, 5547 (1995).
• For use as catalyst in the Stille coupling of arylstannanes, see Tri-n-butyltin chloride, A10746. For examples of the Stille coupling of arylstannanes with aryl triflates to give unsymmetrical biaryls, see: Org. Synth. Coll., 9, 553 (1998). For reviews, see: Adv. Met.-Org. Chem., 5, 1 (1996); Org. React, 50, 1 (1997).
• Catalyst for the carbonylation of benzyl halides with CO in an alcohol, in the presence of a base, e.g. 1,8-Bis(dimethylamino)naphthalene, L00313, to give arylacetic esters: J. Org. Chem., 40, 532 (1975). Similarly, allylic chlorides are carbonylated to give predominantly ?-unsaturated acids at atmospheric pressure: Chem. Lett., 957 (1988), and bromo alkanols give lactones: J. Am. Chem. Soc., 102, 4193 (1980):
  
• Also catalyzes the low-pressure carbonylative cross-coupling of arylboronic acids with iodoarenes to give unsymmetrical biaryl ketones: Tetrahedron Lett., 34, 7595 (1993); J. Org. Chem., 63, 4726 (1998).
• Catalyzes the exclusively cis-addition of Tri-n-butyltin hydride, A13298, to alkynes at room temperature, to give vinylstannanes in good yield: J. Org. Chem., 55, 1857 (1990):
  
• In combination with acetic anhydride and triphenylphosphine, catalyzes the selective conversion of carboxylic acids to 1-alkenes of one less carbon atom: J. Org. Chem., 58, 29 (1993).