Cycloocta-1,5-diene dichloropalladium

Base Information

• Chemical Name: Cycloocta-1,5-diene dichloropalladium
• CAS No.: 12107-56-1
• Deprecated CAS: 12193-11-2
• Molecular Formula: C8H12Cl2Pd
• Molecular Weight: 285.509
• Hs Code.: 28439000
• European Community (EC) Number: 235-161-8
• UNII: SK5GRF586M
• Mol file: 12107-56-1.mol

Synonyms:12107-56-1;SK5GRF586M;NSC 169973;EINECS 235-161-8;Cycloocta-1,5-diene dichloropalladium;Palladium, dichloro(1,5-cyclooctadiene)-;C8H12Cl2Pd;C8-H12-Cl2-Pd;Dichloro((1,2,5,6-eta)-cycloocta-1,5-diene)palladium;dichloro[(1,2,5,6-eta)-cycloocta-1,5-diene]palladium;UNII-SK5GRF586M;1,5-Cyclooctadiene, palladium complex;AKOS016003871;NSC-169973;1,5-Cyclooctadienepalladium(II) Dichloride;D2604;Dichloro[(1,2,5,6-eta)-1,5-cyclooctadiene]palladium

Chemical Property of Cycloocta-1,5-diene dichloropalladium

Chemical Property:

• Appearance/Colour: brown-black crystals
• Vapor Pressure: 4.25mmHg at 25°C
• Melting Point: 210 °C (dec.)(lit.)
• Boiling Point: 153.5 °C at 760 mmHg
• Flash Point: 31.7 °C
• PSA: 0.00000
• LogP: 4.05180
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Hygroscopic
• Solubility.: Soluble in dichloromethane
• Water Solubility.: insoluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 283.93509
• Heavy Atom Count: 11
• Complexity: 72.6

Purity/Quality:

99% ^*data from raw suppliers

Dichloro[(1,2,5,6-η)-1,5-cyclooctadiene]-palladium ^*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:

• Chemical Classes: Metals -> Organic Compounds, Metal Salts
• Canonical SMILES: C1CC=CCCC=C1.[Cl-].[Cl-].[Pd+2]
• Isomeric SMILES: C1/C=C\CC/C=C\C1.[Cl-].[Cl-].[Pd+2]
• Uses: Dichloro(1,5-cyclooctadiene)palladium(II) is used as catalyst for C-C bond and C-N formation, used in Heck coupling of alkynes with alkenes, Suzuki cross-coupling of aryl bromides , allylic substitution of oximes with allylic acetate and methoxycarbonylation of iodobenzene. Dichloro(1,5-cyclooctadiene)palladium(II) is a commonly used catalyst to protect alcohols as acetals by treating with 2-benzyloxy-1-propene; to synthesize bicyclooctanes from diethyl malonate and in alkene carbonylation. It can also be used to catalyze the Heck coupling of nonactivated vinyl phosphates with electron deficient alkenes; the synthesis of benzo[b]thiophenes from thioenols and to prepare an active catalyst for Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions.

Technology Process of Cycloocta-1,5-diene dichloropalladium

There total 19 articles about Cycloocta-1,5-diene dichloropalladium 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%

Pd(C9H14)Cl2 (46059-16-9,32714-63-9) + cyclo-octa-1,5-diene (5259-72-3,10060-40-9,111-78-4) → dichloro(cycloocta-1,5-diene)palladium (II) (12107-56-1)

Guidance literature:

In chloroform-d1; byproducts: CND-1,5; exchange reactions complete at 50°C in 43 h; various temp. and time various yields;

DOI:10.1021/ja00401a012

Reference yield: 98.4%

1,5-cis,cis-cyclooctadiene (1552-12-1,111-78-4) + chlorine (7782-50-5) + palladium (7440-05-3) → dichloro(1,5-cyclooctadiene)palladium(II) (12107-56-1)

Guidance literature:

chlorine; palladium⁽⁰⁾; With hydrogenchloride; In water monomer; at 50 ℃; for 2h; under 375.038 Torr; Large scale;

1,5-cis,cis-cyclooctadiene; With sodium chloride; In isopropanol; at 20 ℃; for 4h; Pressure; Temperature; Reagent/catalyst; Large scale;

Reference yield: 98.0%

palladium dichloride + cyclo-octa-1,5-diene (5259-72-3,10060-40-9,111-78-4) → dichloro(1,5-cyclooctadiene)palladium(II) (12107-56-1)

Guidance literature:

palladium dichloride; With hydrogenchloride; In water; at 20 ℃; for 0.166667h; Inert atmosphere;

cyclo-octa-1,5-diene; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.orglett.1c02307

upstream raw materials:

palladium(II) chloride benzonitrile complex

cyclo-octa-1,5-diene

bis(cyclo-octa-1,5-diene)palladium

Chlorotrifluoroethylene

Downstream raw materials:

dichloro bis(acetonitrile) palladium(II)

dichlorobis{(2-methoxyethyl)phenyl(3-trimethoxypropyl)phosphane}palladium(II)

dichlorobis{phenyl(2-tetrahydrofuranylmethyl)(3-trimethoxypropyl)phosphane}palladium(II)

chloro-bis(diphenylphosphinoethyl)aminepalladium(II) chloride

Refernces

• 1、 Díaz-García, Diana,Darbandi, Masih,Gómez-Ruiz, Santiago,Narimani, Ehsan. "Synthesis, characterization and application of pure and decorated with palladium mesoporous cobalt hydroxide hexagonal nanorings". . . Retrieved 2020.
• 2、 Suzaki, Yuji,Kobayashi, Yuka,Tsuchido, Yoshitaka,Osakada, Kohtaro. "Pd-catalyzed Sonogashira coupling in aqueous media. Observation of micelles that contain substrates and catalyst". . p. 106 - 111. Retrieved 2019.
• 3、 Hossain, Abul Monsur Showkot,Balbín, Adriana,Erami, Roghayeh Sadeghi,Prashar, Sanjiv,Fajardo, Mariano,Gómez-Ruiz, Santiago. "Synthesis and study of the catalytic applications in C–C coupling reactions of hybrid nanosystems based on alumina and palladium nanoparticles". . p. 645 - 652. Retrieved 2017.
• 4、 Buchwald, Stephen L.,King, Ryan P.,Krska, Shane W.. "A Neophyl Palladacycle as an Air- And Thermally Stable Precursor to Oxidative Addition Complexes". supporting information. p. 7927 - 7932. Retrieved 2021/10/25.
• 5、 Frei, Angelo,Ramu, Soumya,Lowe, Gabrielle J.,Dinh, Hue,Semenec, Lucie,Elliott, Alysha G.,Zuegg, Johannes,Deckers, Anke,Jung, Nicole,Br?se, Stefan,Cain, Amy K.,Blaskovich, Mark A. T.. "Platinum Cyclooctadiene Complexes with Activity against Gram-positive Bacteria". supporting information. p. 3165 - 3171. Retrieved 2021/07/16.