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917745

Sigma-Aldrich

[Ni(dtbbpy)(H2O)4]Cl2

Synonym(s):

Nickel(2+), tetraaqua[4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-κN1,κN1′]-, chloride

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500 MG
¥14,500
5 G
¥74,400

About This Item

Empirical Formula (Hill Notation):
C18H32Cl2N2NiO4
CAS Number:
2035424-75-8
Molecular Weight:
470.06
MDL number:
MFCD33021751
UNSPSC Code:
12161600
NACRES:
NA.22

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form

powder

Quality Level

100

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

mp

>300 °C

SMILES string

[Ni+2]1([NH]2=CC=C(C=C2C3=CC(=CC=[NH]31)C(C)(C)C)C(C)(C)C)(O)(O)(O)O.C

InChI key

UTKNAEDPSHMNCR-UHFFFAOYSA-J

Related Categories

Application

[Ni(dtbbpy)(H2O)4]Cl2 is a Ni precatalyst used in a series of Ni/photoredox dual catalysis cross-coupling reactions. These transformations include the decarboxylative coupling of oxetanyl amino acids with aryl halides.

Other Notes

Dual Photoredox/Nickel-Catalyzed Conversion of Aryl Halides to Aryl Aminooxetanes: Computational Evidence for a Substrate-Dependent Switch in Mechanism

1,4-Dihydropyridines as Alkyl Radical Precursors: Introducing the Aldehyde Feedstock to Nickel/Photoredox Dual Catalysis

Storage Class Code

11 - Combustible Solids

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

917745-VAR:
917745-5G:4548173371955
917745-500MG:
917745-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV3407
MKCN0073
MKCS6680

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Álvaro Gutiérrez-Bonet et al.
ACS catalysis, 6(12), 8004-8008 (2016-12-19)
A Ni/photoredox dual catalytic cross-coupling is disclosed in which a diverse range of (hetero)aryl bromides are used as electrophiles, with 1,4-dihydropyridines serving as precursors to Csp3-centered alkyl radical coupling partners. The reported method is characterized by its extremely mild reaction
Dual Photoredox/Nickel-Catalyzed Conversion of Aryl Halides to Aryl Aminooxetanes: Computational Evidence for a Substrate-Dependent Switch in Mechanism.
Kolahdouzan K, et al.
ACS Catalysis, 10(1), 405-411 (2020)

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