Dichlorobis(triphenylphosphine)palladium

Base Information

• Chemical Name: Dichlorobis(triphenylphosphine)palladium
• CAS No.: 13965-03-2
• Molecular Formula: C36H30Cl2P2Pd
• Molecular Weight: 701.908
• Hs Code.: 28439090
• European Community (EC) Number: 237-744-2,233-495-9
• NSC Number: 122924
• Wikipedia: Bis(triphenylphosphine)palladium_chloride
• Mol file: 13965-03-2.mol

Synonyms:bis(triphenylphosphino)palladium dichloride;Bis(triphenylphosphine)dichloropalladium;Dichlorobis(triphenylphosphine)palladium;Bis(triphenylphosphine)palladium(II) dichloride;C36H30Cl2P2Pd;13965-03-2;C36-H30-Cl2-P2-Pd;bis(triphenylphosphine]palladium (II) chloride;Bis(Triphenylphosphine)palladium (II) chloride;Bis(triphenylphosphine)palladium chloride;bis(triphenylphosphine)palladium(ii)chloride;bis(triphenylphosphine)palladium(ii) chloride;bis(triphenylphosphine)palladium(ii)dichloride;Palladium(II)bis(triphenylphosphine) dichloride;bis(triphenylphosphine) palladiuml(ii) dichloride;BIS(TRIPHENYLPHOSPHINE)DICHLOROPALLADIUM(II);TRANS-BIS(TRIPHENYLPHOSPHINE)PALLADIUM(II)CHLORIDE;pdcl2(tpp)2;(Ph3P)2PdCl2;(PPh3)2PdCl2;Pd(Ph3P)2Cl2;(Ph3P)2 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Chemical Property of Dichlorobis(triphenylphosphine)palladium

Chemical Property:

• Appearance/Colour: Yellow crystalline powder
• Vapor Pressure: 0Pa at 25℃
• Melting Point: 260 °C
• Boiling Point: 360 °C at 760 mmHg
• Flash Point: 181.7 °C
• PSA: 27.18000
• LogP: 8.26860
• Storage Temp.: Store below +30°C.
• Sensitive.: Hygroscopic
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly, Heated), Methanol (Slightly,
• Water Solubility.: Insoluble in water. Soluble in benzene, and toluene.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 6
• Exact Mass: 702.03911
• Heavy Atom Count: 41
• Complexity: 490

Purity/Quality:

99% ^*data from raw suppliers

Dichlorobis(triphenylphosphine)Palladium(II) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-22-40-19
• Safety Statements: 37/39-26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)[PH+](C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)[PH+](C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl
• General Description: **Null** (No relevant content about *Bis(triphenylphosphine)palladium(II) chloride* is described in the provided abstracts.)

Technology Process of Dichlorobis(triphenylphosphine)palladium

There total 141 articles about Dichlorobis(triphenylphosphine)palladium which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

hydrogenchloride (7647-01-0,15364-23-5) + palladium (7440-05-3) + triphenylphosphine (603-35-0) → bis-triphenylphosphine-palladium(II) chloride (13965-03-2)

Guidance literature:

hydrogenchloride; palladium; With aqua regia; at 80 ℃;

triphenylphosphine; In ethanol; at 70 ℃;

In ethanol; at 70 ℃; for 1h; Temperature; Solvent;

Reference yield: 95.0%

bis(benzonitrile)palladium(II) dichloride (15617-18-2,39958-10-6,14220-64-5) → bis-triphenylphosphine-palladium(II) chloride (13965-03-2)

Guidance literature:

With triphenylphosphine; In chloroform; isolation by filtration;

DOI:10.1021/ja00211a020

Reference yield: 95.0%

dihydrogen decachloro decaborate + palladium dichloride → bis-triphenylphosphine-palladium(II) chloride (13965-03-2) + [(Ph3P)4Pd2Cl2]closo-B10Cl10

Guidance literature:

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.;

upstream raw materials:

triphenylphosphine

trans-[Pd(triphenylphosphine)2(N₄CPh)2]

benzoyl chloride

tetrachloropalladium anion

Downstream raw materials:

bis(1,2-bis(diphenylphosphinoethynyl)benzene)palladium⁽⁰⁾

(E)-3,5-diphenylpent-2-en-4-ynoic acid methyl ester

N-(tert-butoxycarbonyl)4-(2-thiazolyl)-L-phenylalanine methyl ester

2-amino-3,5-diphenyl-pyridine

Refernces

A facile palladium-catalyzed route to 2,5,7-trisubstituted indoles

10.1016/j.tet.2015.10.002

The study presents a facile and general method for synthesizing 2,5,7-trisubstituted indoles, which are significant in pharmaceuticals and natural compounds due to their biological activity. The researchers utilized a one-pot Sonogashira cross-coupling reaction followed by a palladium-catalyzed cyclization to construct the indole rings from readily available 2-bromo-6-iodo-4-substituted and 2-bromo-4-chloro-6-iodoanilines. Further functionalization at the C7 and C5 positions was achieved through alkynylations, Suzuki-Miyaura cross-couplings, and Buchwald-Hartwig C-N bond forming reactions. The methodology offers high yields, simplicity, and versatility, making it valuable for the synthesis of biologically active compounds. The study also includes one-pot protocols for the synthesis of these complex indole derivatives, enhancing the efficiency of the process.

Synthesis, cleavage, and antifungal activity of a number of novel, water-soluble ester prodrugs of antifungal triazole CS-758

10.1016/j.bmcl.2009.04.135

The research focuses on the synthesis, cleavage, and antifungal activity of novel, water-soluble ester prodrugs of the antifungal triazole CS-758, aimed at developing an injectable antifungal agent for severe deep mycoses in hospitalized patients. The study describes the synthesis of several esters of CS-758, with a particular emphasis on phosphoryl ester 1a, which demonstrated good water solubility and efficient conversion to CS-758 in human liver microsomes and rats. The experiments involved various chemical reactions, including phosphorylation, oxidation, and esterification, utilizing reagents such as diallyl diisopropylphosphoramidite, t-butyl hydroperoxide, and bis(triphenylphosphine)dichloropalladium. The synthesized compounds were analyzed for their water solubility and ability to release CS-758 in vitro using human plasma and liver microsomes, and in vivo by administering the prodrugs to rats and measuring the bioavailability and conversion to CS-758. The antifungal activity of the prodrug 1a was evaluated in a murine systemic Candida albicans infection model, showing comparable or slightly superior effects to orally administered CS-758.

On the Chemistry of Pyrazolylalkines; Pyrazoles II.

10.1007/BF00809599

The research focuses on the chemistry of pyrazolylalkines, specifically the palladium-catalyzed reactions of 1-benzoyl-4-iodopyrazole with mono-substituted acetylenes, which provides a convenient access to cross-coupled products. The study aims to simplify the synthesis of 4-alkinylsubstituted pyrazoles, which are of interest as precursors for compounds with alcohol-dehydrogenase-inhibiting effects. The researchers report a method that allows for the palladium-catalyzed coupling of the C-4 of a pyrazole system with monosubstituted alkenes without the use of the 2,4,6-trimethylbenzoyl protecting group. They also share attempts at Hg(II)-catalyzed hydration of 4-alkinyl-substituted 1H-pyrazoles to synthesize 4-pyrazolylketones. The chemicals used in the process include 1-benzoyl-4-iodopyrazole, mono-substituted acetylenes, triethylamine, bis-(triphenylphosphin)-palladium(II)-chlorid, and copper(I)-iodid, among others. The conclusions drawn from the study highlight the efficiency of the methanolic removal of protecting groups and the regiospecificity of the Hg(II)-catalyzed hydration reactions, which yield the desired ketones with good yields and without the formation of isomers.

Three-component synthesis of N-boc-4-iodopyrroles and sequential one-pot alkynylation

10.1021/ol900581a

The research focuses on the development of an efficient one-pot three-component synthesis of 2-substituted N-Boc-4-iodopyrroles, which are valuable synthetic building blocks for pharmaceuticals and materials science. The purpose of this study was to create a mild and practical method for synthesizing these compounds using a Pd/Cu-catalyzed process that can be easily upscaled to produce multigrams of the desired product. The researchers successfully developed a method that involves the coupling of (hetero)aryl-, alkenyl-, and selected alkyl-substituted acid chlorides with N-Boc-protected propargylamine to produce ynones, which are then converted in a one-pot fashion to 2-substituted N-Boc-4-iodopyrroles. The process was found to be quite general with respect to the underlying acid chlorides, tolerating a variety of substituents. The study also demonstrated preliminary examples of a sequential coupling-addition-cyclocondensation-coupling sequence to 4-alkynyl-N-Boc-pyrroles in good yields, showcasing the versatility of this one-pot multicomponent strategy. Key chemicals used in the process include PdCl2(PPh3)2, CuI, triethylamine, acid chlorides, N-Boc-protected propargylamine, sodium iodide, and toluene-4-sulfonic acid monohydrate, among others.

Synthesis of 2-alkynyl 1,3,4-oxadiazoles by palladium-catalyzed cross- coupling reaction 1

10.1055/s-0034-1378361

The research focuses on the efficient synthesis of 2-alkynyl 1,3,4-oxadiazoles, which are significant in pharmaceutical and material sciences due to their potential bioactivity and applications in organic electronics. The study reports the first application of the Sonogashira reaction for the preparation of these oxadiazole derivatives. The experiments involved the palladium-catalyzed cross-coupling of 2-bromo-1,3,4-oxadiazoles with terminal alkynes under Sonogashira conditions, utilizing PdCl2(PPh3)2 and CuI as catalysts, and Et3N as a base in DMF solvent at 60°C. The reaction conditions were optimized to achieve high yields of products without side products. Various reactants, including different 2-bromo-1,3,4-oxadiazoles with electron-donating or electron-withdrawing groups and a range of terminal alkynes with aromatic, heteroaromatic, or aliphatic moieties, were used. The synthesized products were characterized using spectroscopic data, including IR, 1H NMR, 13C NMR, and ESI-MS, and compared with known compounds to confirm their structures.

Branching out at C-2 of septanosides. Synthesis of 2-deoxy-2-C-alkyl/aryl septanosides from a bromo-oxepine

10.3762/bjoc.8.59

The research aimed on the synthesis of 2-deoxy-2-C-alkyl/aryl septanosides, which are unnatural seven-membered cyclic sugars, using a common bromo-oxepine intermediate. The purpose of the study was to explore the reactivity of bromo-oxepine in the synthesis of septanosides, branching out at C-2, through C–C bond formation with alkyl and aryl substituents. The researchers utilized C–C bond forming organometallic reactions such as Heck, Suzuki, and Sonogashira coupling reactions with various substrates including acrylates, arylboronic acids, and alkynes. The conclusions drawn from the study demonstrated the effective application of bromo-oxepine for the preparation of previously unknown 2-deoxy-2-C-alkyl/aryl septanoside derivatives, highlighting the scope of seven-membered bromo-oxepines as useful substrates for generating these septanosides. Key chemicals used in the process included phenylboronic acid, substituted phenylboronic acids, acetylenes, Pd(OAc)2, Pd(PPh3)2Cl2, CuI, and various acrylates and styrenes.