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Sigma-Aldrich

Ni(COD)(DQ)

≥95%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C18H24NiO2
CAS Number:
Molecular Weight:
331.08
MDL number:
UNSPSC Code:
12352103
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

Assay

≥95%

form

powder

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

parameter

temperature stable

mp

227 °C (decomposition)

SMILES string

[Ni](C)C.O=C2C(=C(C(=O)C(=C2C)C)C)C.C1CCC\C=C/CC1

InChI key

PRUJUYLPWIUASG-ZMKTYRQVSA-N

Application

Ni(COD)(DQ), as shown by the Engle lab, is an air- and thermally stable Ni(0) precatalyst. This 18-electron complex has a unique stability profile allowing for easy reaction setup outside an inert atmosphere. Transformations such as the Suzuki-Miyaura coupling, borylation of aryl halides, and alkene hydroarylation have been demonstrated.

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Pictograms

Health hazardExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Carc. 2 - Skin Sens. 1 - STOT RE 1

Target Organs

Lungs

Storage Class Code

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

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Van T Tran et al.
Angewandte Chemie (International ed. in English) (2020-02-18)
We report that Ni(COD)(DQ) (COD=1,5-cyclooctadiene, DQ=duroquinone), an air-stable 18-electron complex originally described by Schrauzer in 1962, is a competent precatalyst for a variety of nickel-catalyzed synthetic methods from the literature. Due to its apparent stability, use of Ni(COD)(DQ) as a

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

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    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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  2. 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/449/386/product-dating-information-mk.pdf

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