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:
Molecular Weight:
275.06
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352202
EC Number:
215-072-0
MDL number:
Quality Level
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
Application
Reactant for:
Catalyst 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.
Catalyst for the cycloaddition of 1,3-dienes.
signalword
Danger
hcodes
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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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.
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
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