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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:
Poids moléculaire :
275.06
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352202
ID de substance PubChem :
Nomenclature NACRES :
NA.22
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Niveau de qualité

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

Application

Catalyst for the cycloaddition of 1,3-dienes.[1]
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.[2]

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Pictogrammes

FlameHealth hazardExclamation mark

Mention d'avertissement

Danger

Mentions de danger

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


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Consulter la Bibliothèque de documents

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
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
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.
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

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

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

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

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

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