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:

97% ^*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]
• General Description: BIS(1,5-CYCLOOCTADIENE)NICKEL(0) (Ni(COD)?) serves as a key catalyst in intramolecular cyclization reactions of α,ω-dienals, facilitating the formation of (π-allyl)Ni intermediates that undergo stereoselective 'metallo-ene'-type cyclizations. The reactivity of Ni(COD)? can be hindered by strongly coordinating heteroatoms or sterically demanding substituents that disrupt the π-allyl complex formation. BIS(1,5-CYCLOOCTADIENE)NICKEL(0) is widely used in carbonylative and noncarbonylative transformations to generate diverse cycloadducts upon methanol quenching.

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:

C₂₁H₂₄N₂Ni

Ni⁽⁰⁾(1,2-bis(diphenylphosphino)ethane)2

bis(1,3-bis(diphenylphosphino)propane)nickel⁽⁰⁾

C₂₆H₃₈NNiO₃PS

Refernces

Intramolecular Ni-mediated cyclizations with α,ω-dienals

10.1002/1099-0690(200104)2001:7<1359::AID-EJOC1359>3.0.CO;2-7

The study involves the preparation of fifteen α,ω-dienals and one α-en-ω-ynal, which were treated with Ni(COD)2/TMSCl under carbonylative and noncarbonylative conditions, followed by methanol quenching of the resulting metal intermediates to afford different types of cycloadducts. The research concludes that the reaction proceeds through an intermediate (π-allyl)Ni complex, which cyclizes in a 'metallo-ene'-type reaction, and that the process is stereoselective but can be blocked by the presence of highly coordinating heteroatoms or substituents that interact sterically with the initially formed π-allyl complex.