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13965-03-2

Basic Information
CAS No.: 13965-03-2
Name: Bis(triphenylphosphine)palladium(II) chloride
Article Data: 119
Molecular Structure:
Molecular Structure of 13965-03-2 (Bis(triphenylphosphine)palladium(II) chloride)
Formula: C36H30Cl2P2Pd
Molecular Weight: 701.908
Synonyms: Bis(triphenylphosphine)dichloropalladium;Bis(triphenylphosphine)palladiumdichloride;Bis(triphenylphosphine)palladium(II) dichloride;NSC 122924;Palladiumbis(triphenylphosphine) dichloride;
EINECS: 237-744-2
Melting Point: 260 °C
Boiling Point: 360 °C at 760 mmHg
Flash Point: 181.7 °C
Solubility: Insoluble in water. Soluble in benzene, and toluene.
Appearance: Yellow crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 36/37/38-22
Safety: 37/39-26
PSA: 27.18000
LogP: 8.26860
Synthetic route
7647-01-0

hydrogenchloride

7440-05-3

palladium

603-35-0

triphenylphosphine

13965-03-2

bis-triphenylphosphine-palladium(II) chloride

Conditions
ConditionsYield
Stage #1: hydrogenchloride; palladium With aqua regia at 80℃;
Stage #2: triphenylphosphine In ethanol at 70℃;
Stage #3: In ethanol at 70℃; for 1h; Temperature; Solvent;
100%
15617-18-2, 39958-10-6, 14220-64-5

bis(benzonitrile)palladium(II) dichloride

13965-03-2

bis-triphenylphosphine-palladium(II) chloride

Conditions
ConditionsYield
With triphenylphosphine In chloroform isolation by filtration;95%
With triphenylphosphine In not given (dry N2); dry and deoxygenated solvents; addn. of 2.2 equiv. of PPh3 to Pd-compd.; filtration;95%

dihydrogen decachloro decaborate

palladium dichloride

A

13965-03-2

bis-triphenylphosphine-palladium(II) chloride

[(Ph3P)4Pd2Cl2]closo-B10Cl10

Conditions
ConditionsYield
With PPh3 In ethanol; water molar ratio borane:Pd:PPh3=1:2:4, 70°C, 2 h (pptn.); filtration, washing (H2O, EtOH, ether); extn. of PdCl2(PPh3)2 (toluene);elem. anal.;A n/a
B 95%

tetrachloropalladium anion

603-35-0

triphenylphosphine

13965-03-2

bis-triphenylphosphine-palladium(II) chloride

Conditions
ConditionsYield
In neat (no solvent) at 20℃; Milling;92%
157319-21-6, 114403-39-3

trans-bis(trifluoromethanesulfonate) bis(triphenylphosphine)palladium trihydrate

13965-03-2

bis-triphenylphosphine-palladium(II) chloride

Conditions
ConditionsYield
With sodium chloride In water; acetonitrile Pd-compound in CH3CN was treated with aq. NaCl;91%

palladium dichloride

13965-03-2

bis-triphenylphosphine-palladium(II) chloride

Conditions
ConditionsYield
With triphenylphosphine excess of PPh3;90%
With PPh3; H2O In dimethyl sulfoxide heating a mixt. of PdCl2, PPh3 and water in DMSO under Ar (140°C) yielding a yellow-orange soln., cooling (room temp.), pptn.; filtration, washing (Et2O), drying (vac.);90%
With triphenylphosphine In N,N-dimethyl-formamide Addn. of 2.4 equiv. of PPh3 to DMF soln. of PdCl2 at 140°C.; Cooling, collecting the resultant ppt.;
14221-01-3

tetrakis(triphenylphosphine) palladium(0)

10026-04-7, 53609-55-5

tetrachlorosilane

13965-03-2

bis-triphenylphosphine-palladium(II) chloride

Conditions
ConditionsYield
mixt. of compds. heated at 60 °C for 14 h, under N2; volatiles collected, residue washed with Et2O;89%
21264-30-2, 90243-59-7, 14592-56-4

dichloro bis(acetonitrile) palladium(II)

603-35-0

triphenylphosphine

13965-03-2

bis-triphenylphosphine-palladium(II) chloride

Conditions
ConditionsYield
In dichloromethane Inert atmosphere; Schlenk technique;89%
603-35-0

triphenylphosphine

palladium dichloride

13965-03-2

bis-triphenylphosphine-palladium(II) chloride

Conditions
ConditionsYield
In benzonitrile at 180℃; for 0.333333h; Inert atmosphere; Schlenk technique;88%
In dichloromethane; acetonitrile at 20℃; for 0.166667h; Inert atmosphere;82%
With carbon monoxide In toluene at 125℃; under 7600.51 Torr; for 4h;50%
14221-01-3

tetrakis(triphenylphosphine) palladium(0)

75-77-4

chloro-trimethyl-silane

13965-03-2

bis-triphenylphosphine-palladium(II) chloride

Conditions
ConditionsYield
byproducts: (Me3Si)2, (Me3Si)3O; mixt. of compds. heated at 60 °C for 4 h, under N2; volatiles collected, residue washed with Et2O; elem. anal.;80%
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Specification

The IUPAC name of Bis(triphenylphosphine)palladium(II) chloride is palladium(2+); triphenylphosphane; dichloride. With the CAS registry number 13965-03-2, it is also named as Dichlorobis(triphenylphosphine)palladium. The product's categories are Metal Compounds; Catalysts-Ligands; Catalysts for Organic Synthesis; Classes of Metal Compounds; Homogeneous Catalysts; Metal Complexes; Pd (Palladium) Compounds; Synthetic Organic Chemistry; Transition Metal Compounds. It is yellow crystalline powder which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container and stored in the dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 5.69; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.69; (4)ACD/LogD (pH 7.4): 5.69; (5)ACD/BCF (pH 5.5): 12427.96; (6)ACD/BCF (pH 7.4): 12427.96; (7)ACD/KOC (pH 5.5): 29672.91; (8)ACD/KOC (pH 7.4): 29672.91; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Enthalpy of Vaporization: 58.18 kJ/mol; (13)Vapour Pressure: 4.74E-05 mmHg at 25°C; (14)Rotatable Bond Count: 6; (15)Exact Mass: 700.023462; (16)MonoIsotopic Mass: 700.023462; (17)Heavy Atom Count: 41; (18)Complexity: 202.

Preparation of Bis(triphenylphosphine)palladium(II) chloride: It can be obtained by reaction of palladium(II) chloride with triphenylphosphine.
PdCl2 + 2 PPh3 → PdCl2(PPh3)2

Uses of Bis(triphenylphosphine)palladium(II) chloride: It is used as a catalyst for palladium-catalyzed coupling reactions, e.g. the Suzuki, Kumada, Negishi. It  is an intermediate in the preparation of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4):
PdCl2(PPh3)2 + 2 PPh3 + 2.5 N2H4 → Pd(PPh3)4 + 0.5 N2 + 2 N2H5+Cl-  

When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable gloves and eye/face protection.

People can use the following data to convert to the molecule structure. 
1. Smiles:c1ccc(cc1)P(c1ccccc1)c1ccccc1.c1ccc(cc1)P(c1ccccc1)c1ccccc1.[Pd+2].[ClH-].[ClH-]
2. InChI:InChI=1/2C18H15P.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