Skip to Content
Merck
CN

Key Documents

View All Documentation

244988

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

Synonym(s):

Bis(cyclooctadiene)nickel, Ni(COD)2

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

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
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCP5804
BCCJ4930
BCCH7614
BCCG3760
BCCH5546

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

Articles

Nickel-based Catalysts

Nickel complexes catalyze various synthetic reactions like oxidative addition, C-H activation, and cross-coupling.

Photoredox Iridium Catalyst for SET Cross-Coupling

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

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
View All Related Papers

Global Trade Item Number

SKUGTIN
244988-2G04061825772400