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244988

Sigma-Aldrich

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

Sinónimos:

Bis(cyclooctadiene)nickel, Ni(COD)2

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About This Item

Fórmula empírica (notación de Hill):
C16H24Ni
Número de CAS:
1295-35-8
Peso molecular:
275.06
EC Number:
215-072-0
MDL number:
MFCD00058902
UNSPSC Code:
12352202
PubChem Substance ID:
24854723
NACRES:
NA.22

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

Categorías relacionadas

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.

Related product

Referencia del producto
Descripción
Precios

06693

Timestrip Plus™ -20 °C

912794

Ni(COD)(DQ), ≥95%

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_germany

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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Certificados de análisis (COA)

Lot/Batch Number
BCCF6273
BCCF2521
BCCD5458
BCCC8700
BCCC7214

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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
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
Ruimao Hua et al.
Organic letters, 9(2), 263-266 (2007-01-16)
Allylic sulfides add to alkynes in the presence of nickel complexes efficiently to afford thio-1,4-dienes regio- and stereoselectively. Functional groups such as alkoxy, siloxy, hydroxy, carboalkoxy, chloro, and cyano groups are tolerated. A mechanism that involves a pi-allyl nickel intermediate
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)
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Nickel and Nickel-based Compounds (Complexes) as a Catalyst

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Global Trade Item Number

Número de referencia del producto (SKU)GTIN
244988-2G4061825772400

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