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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
MDL number:
MFCD32672301
UNSPSC Code:
12352101
NACRES:
NA.22

Assay

≥95%

form

powder

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

mp

322-326 °C

SMILES string

[Ni+2].P(CCP(c4ccccc4)c3ccccc3)(c2ccccc2)c1ccccc1.[Br-].[Br-]

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

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.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

913278-VAR:
913278-500MG:4548173366852
913278-BULK:

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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-based Catalysts

Nickel complexes catalyze various synthetic reactions like oxidative addition, C-H activation, and cross-coupling.

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