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223689

Bis(benzonitrile)palladium(II) chloride

greener alternative

95%, powder

Synonym(s):

Benzonitrile, palladium complex, Bis(benzonitrile)dichloropalladium(II), Bis(benzonitrile)palladium(II) chloride, Bis(phenylnitrile)dichloropalladium, Dibenzonitrilepalladium dichloride, Dichlorobis(benzonitrile)palladium, Dichlorobis(benzonitrile)palladium(II), Dichlorobis(phenyl cyanide)palladium, Palladium dichloride bis(benzonitrile), Palladium(II) chloride bis(benzonitrile) complex

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$96.20

10 G

$885.00

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About This Item

Linear Formula:
(C6H5CN)2PdCl2
CAS Number:
Molecular Weight:
383.57
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12161600
EC Number:
238-085-3
MDL number:
Beilstein/REAXYS Number:
3981730

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Product Name

Bis(benzonitrile)palladium(II) chloride, 95%

InChI key

WXNOJTUTEXAZLD-UHFFFAOYSA-L

InChI

1S/2C7H5N.2ClH.Pd/c2*8-6-7-4-2-1-3-5-7;;;/h2*1-5H;2*1H;/q;;;;+2/p-2

SMILES string

Cl[Pd]Cl.N#Cc1ccccc1.N#Cc2ccccc2

assay

95%

form

powder

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: catalyst

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

131 °C (lit.)

greener alternative category

Quality Level

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1 of 4

This Item
225657446319323373
reaction suitability

core: palladium, reaction type: Heck Reaction, reaction type: Negishi Coupling, reaction type: Stille Coupling, reagent type: catalyst, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Sonogashira Coupling, reaction type: Suzuki-Miyaura Coupling, reaction type: Hiyama Coupling

reaction suitability

core: palladium, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: catalyst

reaction suitability

core: palladium, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: catalyst

reaction suitability

core: palladium, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: catalyst

assay

95%

assay

99%

assay

99.99%

assay

99.995%

form

powder

form

powder

form

powder

form

powder

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

mp

131 °C (lit.)

mp

-

mp

-

mp

678-680 °C (lit.)

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

greener alternative product characteristics

-

greener alternative product characteristics

-

Application

Bis(benzonitrile)palladium(II) chloride can be used as a catalyst:
  • For greener amine synthesis from terminal olefins by Wacker oxidation, followed by transfer hydrogenation of the resultant imine.
  • In cross-coupling reactions[1][2] and α-O-glycosidation.[3]

Formal anti-Markovnikov hydroamination of terminal olefins

General description

Bis(benzonitrile)palladium(II) chloride is a coordination compound used as a catalyst in the Suzuki Cross-Coupling reaction.[4]


We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Find details here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Brandon P Schuff et al.
Organic letters, 9(16), 3173-3176 (2007-07-10)
A novel method for palladium-catalyzed stereoselective formation of alpha-O-glycosides has been developed. This strategy relies on the palladium-biaryl phosphine catalyst-glycal donor complexation to control the anomeric selectivity. It does not depend on the nature of the protecting groups on the
Wei Shi et al.
Chemical communications (Cambridge, England), (23), 2342-2344 (2007-09-12)
A direct alkynylation of readily available alpha-halo esters and amides with high yields is described herein; a distinct switch from diyne formation to alkynylation products was attained under neutral conditions.
Catalysts of Suzuki Cross-Coupling Based on Functionalized Hyper-cross-linked Polystyrene: Influence of Precursor Nature
Nemygina N, et al.
Organic Process Research & Development, 20(8), 1453-1460 (2019)
Shih-Chieh Yeh et al.
Polymers, 11(12) (2019-12-11)
A crucial polymer intermediate, 4-[1-(4-hydroxyphenyl)cyclopentyl]-phenol (bisphenol CP), was developed from dicyclopentadiene (DCPD), a key byproduct of the C5 fraction in petrochemicals. On the basis of bisphenol CP, a diamine, 4,4'-((cyclopentane-1,1-diylbis(4,1-phenylene))bis(oxy))-dianiline (cyclopentyl diamine; CPDA) was subsequently obtained through a nucleophilic substitution
Synthesis, 803-803 (1992)

Questions

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    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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