Bis(1,5-cyclooctadiene)nickel

Base Information

• Chemical Name: Bis(1,5-cyclooctadiene)nickel
• CAS No.: 1295-35-8
• Molecular Formula: C16H24Ni
• Molecular Weight: 275.057
• Hs Code.: 29319090
• European Community (EC) Number: 215-072-0
• UN Number: 1325
• Wikipedia: Bis(cyclooctadiene)nickel(0)
• Mol file: 1295-35-8.mol

Synonyms:Bis(1,5-cyclooctadiene)nickel(0);Bis(1,5-cyclooctadiene)nickel;1295-35-8;Ni(COD)2;CCRIS 5973;Nickel, bis(1,5-cyclooctadiene)-;EINECS 215-072-0;Bis(1,5-cyclooctadiene)nickel (0);Bis((1,2,5,6-eta)-1,5-cyclooctadiene)nickel;BIS(1,5-CYCLOOCTADIENE) NICKEL;Bis(cyclooctadiene)nickel(0);MFCD00058902;(1Z,5Z)-cycloocta-1,5-diene;nickel;C16H24Ni;C16-H24-Ni;JRTIUDXYIUKIIE-KZUMESAESA-N;AKOS032949900;Bis(1,5-cyclooctadiene)nickel(0)??;GS-5738;LS-2102;SC10006;BP-11392;bis((1Z,5Z)-cycloocta-1,5-diene) nickel;B3095;CS-0035192;A805947;Bis[(1,2,5,6-.eta.)-1,5-cyclooctadiene]nickel;J-519856;Nickel, bis((1,2,5,6-eta)-1,5-cyclooctadiene)-;Nickel, bis[(1,2,5,6-.eta.)-1,5-cyclooctadiene]-

Chemical Property of Bis(1,5-cyclooctadiene)nickel

Chemical Property:

• Appearance/Colour: Yellow crystals or yellowish green solid.
• Vapor Pressure: 4.25mmHg at 25°C
• Melting Point: 60 °C (dec.)(lit.)
• Boiling Point: 153.5ºC at 760 mmHg
• Flash Point: 31.7ºC
• PSA: 0.00000
• LogP: 5.34560
• Storage Temp.: 0-6°C
• Sensitive.: Air Sensitive
• Water Solubility.: Soluble in benzene, toluene, terahydrofuran, ether, dimethyl formamide, hexamethylphosphoramide, N-methylpyrrolidinone. Insolubl
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 274.123142
• Heavy Atom Count: 17
• Complexity: 72.6
• Transport DOT Label: Flammable Solid

Purity/Quality:

99.0%, ^*data from raw suppliers

Bis(1,5-cyclooctadiene)nickel(0) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F; Xn; T
• Hazard Codes: F,Xn,T
• Statements: 11-40-45-十一月
• Safety Statements: 36/37-45-16-53

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Metals, Organic Compounds
• Canonical SMILES: C1CC=CCCC=C1.C1CC=CCCC=C1.[Ni]
• Isomeric SMILES: C1/C=C\CC/C=C\C1.C1/C=C\CC/C=C\C1.[Ni]
• Uses: Bis(1,5-cyclooctadiene)nickel(0) is used as a catalyst for the cycloaddition of 1,3-dienes and is used to catalyze the addition of allyl phenyl sulfide to alkynes leading to 1,4-dienes. Also, it is involved as a catalyst for asymmetric alpha-arylation and heteroarylation of ketones with chloroarenes, stereoselective borylative ketone-diene coupling, cycloaddition of benzamides with internal alkynes and methyl carboxylation of homopropargylic alcohols.

Technology Process of Bis(1,5-cyclooctadiene)nickel

There total 37 articles about Bis(1,5-cyclooctadiene)nickel 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: 93.5%

bis(acetylacetonate)nickel(II) + diethyl(ethoxy)aluminum (1586-92-1) + cyclo-octa-1,5-diene (5259-72-3,10060-40-9,111-78-4) → bis(1,5-cyclooctadiene)nickel (0) (1295-35-8)

Guidance literature:

In benzene; molar ratio nickel acetylacetonat : cyclooctadiene = 1 : 2.5-5, benzene free from air, reduction between 0 and 5°C, 2 h, and room temp. 15 h;

Reference yield: 93.0%

Ni(2+)*C12H18(2-)=NiC12H18 + cyclo-octa-1,5-diene (5259-72-3,10060-40-9,111-78-4) → bis(1,5-cyclooctadiene)nickel (0) (1295-35-8)

Guidance literature:

byproducts: all-trans-cyclododeca-1,5,9-triene, cis,trans,trans-cyclododeca-1,5,9-triene; 80-90°C, 1.5 h;

Reference yield: 92.0%

bis(acetylacetonate)nickel(II) + cyclo-octa-1,5-diene (5259-72-3,10060-40-9,111-78-4) → bis(1,5-cyclooctadiene)nickel (0) (1295-35-8)

Guidance literature:

With dibutylmagnesium; In diethyl ether; n-heptane; at -40 - 25 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/anie.202110785

upstream raw materials:

isopropylmagnesium bromide

nickel dichloride

cyclo-octa-1,5-diene

tetrabutylammomium bromide

Downstream raw materials:

nickel dibromide

ethene

nickel diacetate

iron pentacarbonyl

Refernces

• 1、 Belderrain, Tomas R.,Knight, D. Andrew,Irvine, Derek J.,Paneque, Margarita,Poveda, Manuel L.,Carmona, Ernesto. "Ethoxycarbonyl-, Cyano- and Methoxy-methyl Complexes of Nickel(II) and their Carbonylation Reactions". . p. 1491 - 1496. Retrieved 1992.
• 2、 Wegner, Susann,Rutz, Christina,Schütte, Kai,Barthel, Juri,Bushmelev, Alexey,Schmidt, Annette,Dilchert, Katharina,Fischer, Roland A.,Janiak, Christoph. "Soft, Wet-Chemical Synthesis of Metastable Superparamagnetic Hexagonal Close-Packed Nickel Nanoparticles in Different Ionic Liquids". . p. 6330 - 6340. Retrieved 2017.
• 3、 Sicard, Alexandre J.,Baker, R. Tom. "Safe and Expeditious Preparation of Ni(cod)2for Same-Day High-Throughput Screening". . p. 2950 - 2952. Retrieved 2020.
• 4、 Schroeder, Wolfgang,Poerschke, Klaus R.. "tmeda-NICKEL-KOMPLEXE. I. (tmeda)Ni(η2-C4H6)2 and 2-C4H6)>2(η2,η2-C4H6)". . p. 385 - 392. Retrieved 1987.
• 5、 Dong, Zhaowen,Bedbur, Katja,Schmidtmann, Marc,Müller, Thomas. "Hafnocene-based Bicyclo[2.1.1]hexene Germylenes - Formation, Reactivity, and Structural Flexibility". . p. 3052 - 3060. Retrieved 2018.
• 6、 Lehmkuhl,Leuchte. "". . p. C30. Retrieved 1970.
• 7、 Chin, Mason T.,H?rner, Gerald,Klein, Axel,Kletsch, Lukas,Sandleben, Aaron,Sch?fer, Sascha,Vicic, David A.,Vogt, Nicolas. "Role of the X Coligands in Cyclometalated [Ni(Phbpy)X] Complexes (HPhbpy = 6-Phenyl-2,2′-bipyridine)". supporting information. p. 1776 - 1785. Retrieved 2021/06/28.