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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:

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

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

Certificate of Analysis

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Certificate of Origin

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