Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

244988

Sigma-Aldrich

Bis(1,5-cyclooctadiene)nickel(0)

Synonym(s):

Bis(cyclooctadiene)nickel, Ni(COD)2

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C16H24Ni
CAS Number:
1295-35-8
Molecular Weight:
275.06
EC Number:
215-072-0
MDL number:
MFCD00058902
UNSPSC Code:
12352202
PubChem Substance ID:
24854723
NACRES:
NA.22

Quality Level

200

reaction suitability

core: nickel
reaction type: Cross Couplings
reagent type: catalyst

parameter

temperature sensitive

mp

60 °C (dec.) (lit.)

storage temp.

−20°C

SMILES string

[Ni].C1CC=CCCC=C1.C2CC=CCCC=C2

InChI

1S/2C8H12.Ni/c2*1-2-4-6-8-7-5-3-1;/h2*1-2,7-8H,3-6H2;/b2*2-1-,8-7-;

InChI key

JRTIUDXYIUKIIE-KZUMESAESA-N

Related Categories

Application

Reactant for:
  • Oxidative addition reactions

Catalyst for:
  • Asymmetric α-arylation and heteroarylation of ketones with chloroarenes
  • Cross-coupling reactions
  • Regioselective and stereoselective carboxylation/cyclization of allenyl aldehydes under a carbon dioxide atmosphere
  • Methyl carboxylation of homopropargylic alcohols
  • Stereoselective borylative ketone-diene coupling
  • Cycloaddition of benzamides with internal alkynes
Catalyst for the cycloaddition of 1,3-dienes.
Used to catalyze the addition of allyl phenyl sulfide to alkynes leading to 1,4-dienes. The reaction with terminal acetylenes proceeds in high yield and high selectivity. A variety of functional groups are tolerated.

related product

Product No.
Description
Pricing

Signal Word

Danger

Hazard Statements

H228,H317,H351,H372

Hazard Classifications

Carc. 2 - Flam. Sol. 1 - Skin Sens. 1 - STOT RE 1

Target Organs

Lungs

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCJ4930
BCCH7614
BCCG3760
BCCH5546
BCCF6273

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

G Eliad Benitez-Medina et al.
Dalton transactions (Cambridge, England : 2003), 48(47), 17579-17587 (2019-11-22)
The nickel-catalyzed N-alkylation of a variety of arylamines via transfer hydrogenation in the absence of pressurized hydrogen and basic or acidic additives was achieved in a tandem reaction. This process was further extended to the C[double bond, length as m-dash]N
Quanyou Feng et al.
Nature communications, 9(1), 1559-1559 (2018-04-21)
Biodegradable polyesters with various tacticities have been synthesized by means of stereoselective ring-opening polymerization of racemic lactide and β-lactones but with limited side-chain groups. However, stereoselective synthesis of functional polyesters remains challenging from O-carboxyanhydrides that have abundant pendant side-chain functional
Tiziana Funaioli et al.
PloS one, 5(5), e10617-e10617 (2010-05-21)
It is well known that, stemming from the mutual interplay between chromophores, circular dichroism (CD) is a powerful technique to deal with structural problems for both the small organic molecule and the biopolymer. However, quantitative interpretations of the spectroscopic and
Journal of the American Chemical Society, 111, 6432-6432 (1989)
Addison N Desnoyer et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 25(20), 5259-5268 (2019-01-30)
The electronic nature of Ni π-complexes is underexplored even though these complexes have been widely postulated as intermediates in organometallic chemistry. Herein, the geometric and electronic structure of a series of nickel π-complexes, Ni(dtbpe)(X) (dtbpe=1,2-bis(di-tert-butyl)phosphinoethane; X=alkene or carbonyl containing π-ligands)
View All Related Papers

Articles

Photoredox Iridium Catalyst for SET Cross-Coupling

Effective Csp2- and Csp-hybridized coupling reactions established for catalysis, expanding to multi-step Csp3-coupling.

Photoredox Iridium Catalyst for SET Cross-Coupling

Effective Csp2- and Csp-hybridized coupling reactions established for catalysis, expanding to multi-step Csp3-coupling.

Photoredox Iridium Catalyst for SET Cross-Coupling

Effective Csp2- and Csp-hybridized coupling reactions established for catalysis, expanding to multi-step Csp3-coupling.

Photoredox Iridium Catalyst for SET Cross-Coupling

Effective Csp2- and Csp-hybridized coupling reactions established for catalysis, expanding to multi-step Csp3-coupling.

See All

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service