244988

Sigma-Aldrich

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

Synonym(s):
Bis(cyclooctadiene)nickel, Ni(COD)2
Empirical Formula (Hill Notation):
C16H24Ni
CAS Number:
Molecular Weight:
275.06
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

reaction suitability

core: nickel
reagent type: catalyst

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

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.

Packaging

2 g in glass bottle

Signal Word

Danger

Hazard Statements

Target Organs

Lungs

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN1325 - class 4.1 - PG 2 - Flammable solids, organic, n.o.s., HI: all

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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...
Tsung-Han Lin et al.
ACS applied materials & interfaces, 9(5), 4948-4955 (2017-01-13)
The race for performance of integrated circuits is nowadays facing a downscale limitation. To overpass this nanoscale limit, modern transistors with complex geometries have flourished, allowing higher performance and energy efficiency. Accompanying this breakthrough, challenges toward high-performance devices have emerged...
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.
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)...
Journal of the American Chemical Society, 111, 6432-6432 (1989)
Articles
Csp2- and Csp-hybridized coupling reactions are established catalytic approaches. However, multi-step Csp3- and Csp2-coupling reactions of boronic acids and related derivatives are still limited by ineffective two-electron transmetalation reactions.
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