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244988

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

Synonym(s):

Bis(cyclooctadiene)nickel, Ni(COD)2

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1 160,00 kr

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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

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InChI key

JRTIUDXYIUKIIE-KZUMESAESA-N

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-;

SMILES string

[Ni].C1CC=CCCC=C1.C2CC=CCCC=C2

reaction suitability

core: nickel, reaction type: Cross Couplings, reagent type: catalyst

parameter

temperature sensitive

mp

60 °C (dec.) (lit.)

storage temp.

−20°C

Quality Level

200

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This Item
213934901166237116
Bis(1,5-cyclooctadiene)nickel(0)

Sigma-Aldrich

244988

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

Bis(triphenylphosphine)dicarbonylnickel

Sigma-Aldrich

213934

Bis(triphenylphosphine)dicarbonylnickel

cis-[2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl](2-methylphenyl)nickel(II) chloride

Sigma-Aldrich

901166

cis-[2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl](2-methylphenyl)nickel(II) chloride

Bis(triphenylphosphine)nickel(II) dichloride synthesis grade

Sigma-Aldrich

237116

Bis(triphenylphosphine)nickel(II) dichloride

reaction suitability

core: nickel, reagent type: catalyst, reaction type: Cross Couplings

reaction suitability

core: nickel, reagent type: catalyst

reaction suitability

core: nickel, reaction type: Cross Couplings, reagent type: catalyst

reaction suitability

core: nickel, reagent type: catalyst

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

mp

60 °C (dec.) (lit.)

mp

206-209 °C (lit.)

mp

>300 °C

mp

250 °C (dec.) (lit.)

parameter

temperature sensitive

parameter

-

parameter

-

parameter

-

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]

related product

Product No.
Description
Pricing

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

1295-35-8

CAS No.

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCJ4930
BCCH7614
BCCG3760
BCCH5546
BCCF6273

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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
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)
Journal of the American Chemical Society, 111, 6432-6432 (1989)
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