palladium(2+) ion bis(triphenylphosphane) dichloride

• ChemBase ID: 126171
• Molecular Formular: C36H30Cl2P2Pd
• Molecular Mass: 701.896922
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 13965-03-2
• EC Number: 237-744-2
• MDL Number: MFCD00009593
• PubChem SID: 162220512
• PubChem CID: 6102075; 84124
• Chemspider ID: 75895
• Wikipedia Title: Bis(triphenylphosphine)palladium(II)_dichloride

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.1066
• LogD (pH = 7.4): 5.1066
• Log P: 5.1066
• Molar Refractivity: 81.6229 cm^3
• Polarizability: 32.34495 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Crystalline; Powder
• Melting Point: ca 310°C dec.

Safety Information

• Storage Warning: Hygroscopic
• RTECS: RT3578000
• Risk Statements: 53
• Safety Statements: 60-61
• TSCA Listed: 否
• GHS Hazard statements: H413
• GHS Precautionary statements: P273-P501A

Product Information

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

REFERENCES

• 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).