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Merck

244988

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

Synonym(s):

Bis(cyclooctadiene)nickel, Ni(COD)2

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About This Item

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

Key Documents

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InChI key

JRTIUDXYIUKIIE-KZUMESAESA-N

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-;

SMILES string

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

reaction suitability

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

parameter

temperature sensitive

mp

60 °C (dec.) (lit.)

storage temp.

−20°C

Quality Level

200

Related Categories

Application

Catalyst for the cycloaddition of 1,3-dienes.
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
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.

signalword

Danger

Hazard Classifications

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

target_organs

Lungs

Storage Class

4.1B - Flammable solid hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ4930
BCCH7614
BCCG3760
BCCH5546
BCCF6273

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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
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
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
Joachim Loup et al.
Angewandte Chemie (International ed. in English), 58(6), 1749-1753 (2018-12-06)
Highly enantioselective nickel-catalyzed alkene endo-hydroarylations were accomplished with full selectivity by organometallic C-H activation. The asymmetric assembly of chiral six-membered scaffolds proved viable in the absence of pyrophoric organoaluminum reagents within an unprecedented nickel/JoSPOphos manifold.
Qiang Gao et al.
Acta biomaterialia, 51, 112-124 (2017-01-31)
Numerous antimicrobial coatings have been developed for biomedical devices/implants, but few can simultaneously fulfill the requirements for antimicrobial and antifouling ability and biocompatibility. In this study, to develop an antimicrobial and antibiofilm surface coating, diblock amphiphilic molecules with antimicrobial and
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