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913278

Sigma-Aldrich

[1,2-Bis(diphenylphosphino)ethane]dibromonickel(II)

≥95%

Synonym(s):

dppeNiBr2

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About This Item

Empirical Formula (Hill Notation):
C26H24Br2NiP2
CAS Number:
14647-21-3
Molecular Weight:
616.92
UNSPSC Code:
12352101
NACRES:
NA.22

Assay

≥95%

form

powder

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

mp

322-326 °C

InChI

1S/C26H24P2.2BrH.Ni/c1-5-13-23(14-6-1)27(24-15-7-2-8-16-24)21-22-28(25-17-9-3-10-18-25)26-19-11-4-12-20-26;;;/h1-20H,21-22H2;2*1H;/q;;;+2/p-2

InChI key

AEGMSHMBRVOLMV-UHFFFAOYSA-L

Application

[1,2-Bis(diphenylphosphino)ethane]dibromonickel(II) is a catalyst for a variety of transformations, including:
  • kumada catalyst-transfer polycondensation
  • oxidation of carboranyl phosphine ligands
  • synthesis of nickel-iron dithiolato hydrides
  • hydroformylation of alcohols
  • Ullmann reactions - homocoupling reactions
  • intramolecular aerobic oxidative amination of alkenes

Other Notes

Synthesis of Highly Substituted Isoquinolone Derivatives by Nickel-Catalyzed Annulation of 2-Halobenzamides with Alkynes

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Pictograms

Health hazardEnvironment
GHS08,GHS09

Signal Word

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1A Inhalation - Muta. 2 - Repr. 1B - Resp. Sens. 1 - Skin Sens. 1 - STOT RE 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL5644

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Chuan-Che Liu et al.
Organic letters, 12(15), 3518-3521 (2010-07-09)
An efficient method for the synthesis of substituted 1(2H)-isoquinolone derivatives via nickel-catalyzed annulation of substituted 2-halobenzamides with alkynes is described. This protocol is successfully applied to the total synthesis of oxyavicine with excellent yield.

Articles

Nickel and Nickel-based Compounds (Complexes) as a Catalyst

Nickel transition metal and its complexes can be used as a catalyst in many synthetic transformations, like oxidative addition, C-H activation, reductive elimination, oxidative cyclization, oligomerization, and in cross-coupling reactions.

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