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903000

[4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine] nickel (II) dichloride

powder or crystals

Synonym(s):

(4,4′-dtbbpy)NiCl2

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500 mg

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$118.00
$88.50

About This Item

Empirical Formula (Hill Notation):
C18H24Cl2N2Ni
CAS Number:
1034901-50-2
Molecular Weight:
398.00
MDL number:
MFCD31807325
UNSPSC Code:
12352101
NACRES:
NA.22

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Product Name

[4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine] nickel (II) dichloride,

form

powder or crystals

reaction suitability

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

mp

>300 °C

SMILES string

CC(C1=CC(C2=CC(C(C)(C)C)=CC=N2)=NC=C1)(C)C.Cl[Ni]Cl

InChI key

PCWIKFRTCXESOT-UHFFFAOYSA-L

Application

[4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine] nickel (II) dichloride can be used as a catalyst in:
  • Decarboxylative arylation of oxo acids.
  • Acylation of ethers.
  • Cross-coupling of aryl bromides with alcohols.

Other Notes

Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids

Photocatalytic α-Acylation of Ethers

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This Item
911534904937237116
[4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine] nickel (II) dichloride

Sigma-Aldrich

903000

[4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine] nickel (II) dichloride

(4,4′-dMeObpy)NiCl2

Sigma-Aldrich

911534

(4,4′-dMeObpy)NiCl2

2,6-Bis(N-pyrazolyl)pyridine nickel (II) dichloride ≥95% anhydrous basis

Sigma-Aldrich

904937

2,6-Bis(N-pyrazolyl)pyridine nickel (II) dichloride

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

-

reaction suitability

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

reaction suitability

core: nickel, reagent type: catalyst

form

powder or crystals

form

powder or crystals

form

powder or crystals

form

solid

mp

>300 °C

mp

>300 °C

mp

107.9-132.4 °C (Decomp)

mp

250 °C (dec.) (lit.)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SHBT2428
SHBN3311
SHBL5154
MKCH6491

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Articles

Nickel-based Catalysts

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

Ir III/Ni II-Metallaphotoredox catalysis: the oxidation state modulation mechanism versus the radical mechanism
Zhu B, et al.
Chemical Communications (Cambridge, England), 54, 5968-5971 (2018)
Lingling Chu et al.
Angewandte Chemie (International ed. in English), 54(27), 7929-7933 (2015-05-28)
The direct decarboxylative arylation of α-oxo acids has been achieved by synergistic visible-light-mediated photoredox and nickel catalysis. This method offers rapid entry to aryl and alkyl ketone architectures from simple α-oxo acid precursors via an acyl radical intermediate. Significant substrate
Photocatalytic α-Acylation of Ethers
Sun Z, et al.
Organic Letters, 19, 3727-3730 (2017)
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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