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244988

Sigma-Aldrich

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

Synonyme(s) :

Bis(cyclooctadiene)nickel, Ni(COD)2

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About This Item

Formule empirique (notation de Hill) :
C16H24Ni
Numéro CAS:
1295-35-8
Poids moléculaire :
275.06
Numéro CE :
215-072-0
Numéro MDL:
MFCD00058902
Code UNSPSC :
12352202
ID de substance PubChem :
24854723
Nomenclature NACRES :
NA.22

Niveau de qualité

200

Pertinence de la réaction

core: nickel
reagent type: catalyst

Capacité de réaction

reaction type: Cross Couplings

Paramètres

temperature sensitive

Pf

60 °C (dec.) (lit.)

Température de stockage

−20°C

Chaîne SMILES 

[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-;

Clé InChI

JRTIUDXYIUKIIE-KZUMESAESA-N

Catégories apparentées

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.

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

06693

Timestrip Plus™ -20 °C

912794

Ni(COD)(DQ), ≥95%

Pictogrammes

FlameHealth hazardExclamation mark
GHS02,GHS08,GHS07

Mention d'avertissement

Danger

Mentions de danger

H228,H317,H351,H372

Classification des risques

Carc. 2 - Flam. Sol. 1 - Skin Sens. 1 - STOT RE 1

Organes cibles

Lungs

Code de la classe de stockage

4.1B - Flammable solid hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Faites votre choix parmi les versions les plus récentes :

Certificats d'analyse (COA)

Lot/Batch Number
BCCF6273
BCCF2521
BCCD5458
BCCC8700
BCCC7214

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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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