Chloro(1,5-cyclooctadiene)iridium(I) dimer

Base Information

• Chemical Name: Chloro(1,5-cyclooctadiene)iridium(I) dimer
• CAS No.: 12112-67-3
• Molecular Formula: C16H24Cl2Ir2
• Molecular Weight: 671.713
• Hs Code.: 28439000
• European Community (EC) Number: 235-170-7
• DSSTox Substance ID: DTXSID00923689
• Wikipedia: Cyclooctadiene_iridium_chloride_dimer
• Mol file: 12112-67-3.mol

Synonyms:Bis(1,5-cyclooctadiene)diiridium(I) dichloride;

Chemical Property of Chloro(1,5-cyclooctadiene)iridium(I) dimer

Chemical Property:

• Appearance/Colour: red-orange solid
• Vapor Pressure: 4.25mmHg at 25°C
• Melting Point: 205 °C (dec.)(lit.)
• Boiling Point: 153.5ºC at 760 mmHg
• Flash Point: 31.7ºC
• PSA: 0.00000
• LogP: 6.72460
• Storage Temp.: 2-8°C
• Water Solubility.: insoluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 670.04902
• Heavy Atom Count: 20
• Complexity: 72.6

Purity/Quality:

99% ^*data from raw suppliers

Bis(1,5-cyclooctadiene)diiridium(I) dichloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Ir].[Ir]
• Isomeric SMILES: C1/C=C\CC/C=C\C1.C1/C=C\CC/C=C\C1.[Cl-].[Cl-].[Ir].[Ir]
• General Description: Chloro(1,5-cyclooctadiene)iridium(I) dimer, also known as bis(1,5-cyclooctadiene)diiridium(I) dichloride, is an organoiridium compound that serves as a catalyst in polymerization reactions, such as the polymerization of phenylacetylene, where it minimizes oligomeric byproducts. Chloro(1,5-cyclooctadiene)iridium(I) dimer demonstrates catalytic activity in solvents like THF, chloroform, and benzene, with enhanced performance in NEt₃. Spectroscopic studies suggest the formation of monomeric iridium-solvent adducts as active species in the reaction. Additionally, its dimeric structure facilitates oxidative addition reactions, as seen in kinetic studies with iodomethane, where it follows both direct and solvent-assisted pathways. Chloro(1,5-cyclooctadiene)iridium(I) dimer's reactivity is influenced by the diene ligand, which plays a role in stabilizing the catalyst and mediating its deactivation over time.

Technology Process of Chloro(1,5-cyclooctadiene)iridium(I) dimer

There total 16 articles about Chloro(1,5-cyclooctadiene)iridium(I) dimer 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: 99.5%

iridium(III) chloride + cyclo-octa-1,5-diene (5259-72-3,10060-40-9,111-78-4) → bis(1,5-cyclooctadiene)diiridium(I) dichloride (12112-67-3)

Guidance literature:

With hydrazine hydrate; In water; at 90 ℃; Reagent/catalyst; Temperature;

Reference yield: 99.5%

cyclo-octa-1,5-diene (5259-72-3,10060-40-9,111-78-4) → bis(1,5-cyclooctadiene)diiridium(I) dichloride (12112-67-3)

Guidance literature:

With sodium tetrahydroborate; In water; at 80 ℃;

Reference yield: 99.5%

cyclo-octa-1,5-diene (5259-72-3,10060-40-9,111-78-4) → bis(1,5-cyclooctadiene)diiridium(I) dichloride (12112-67-3)

Guidance literature:

With hydrazine hydrate; In water; at 90 ℃;

upstream raw materials:

cyclo-octa-1,5-diene

1,5-cis,cis-cyclooctadiene

iridium tetrachloride monohydrate

Downstream raw materials:

IrCl(1,5-cyclooctadiene)(1,3-bis(diphenylphosphino)propane)

η4-1,5-cyclooctadiene-μ-2,4-pentanedionato-iridium(I)

[Ir(I)(salicylidenephenyliminato)(1,5-cyclooctadiene)]

[Ir(III)(η(3)-CH2CHCHPh)(Cl)2(η(4)-1,5-COD)]

Refernces

Iridium-catalyzed selective hydrogenation of 3-hydroxypyridinium salts: A facile synthesis of piperidin-3-ones

10.1021/acs.orglett.5b00276

The research focuses on the development of a selective hydrogenation method for synthesizing piperidin-3-ones, which are important intermediates in the production of pharmaceutical agents and natural products. The study utilizes a homogeneous iridium catalyst to hydrogenate 3-hydroxypyridinium salts, yielding 2- and 4-substituted piperidin-3-one derivatives with high yields and chemoselectivity. The experiments involved screening various catalysts, solvents, and bases to optimize reaction conditions. Key reactants included 2-phenylpyridin-3-ol as a model substrate and [Ir(COD)Cl]2 as the catalyst, with triphenylphosphine (PPh3) as the optimal ligand and sodium bicarbonate as the base. The reaction was conducted in dichloroethane (DCE) solvent under 600 psi of hydrogen pressure at 50°C for 20 hours. The analyses used to evaluate the reaction included 1H NMR to determine conversion rates and product ratios, as well as isolated yields to assess the efficiency of the process. The optimized conditions led to full conversion and high selectivity for the desired piperidin-3-one products, with further scalability demonstrated through gram-scale experiments.

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