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223689

Sigma-Aldrich

Bis(benzonitrile)palladium(II) chloride

greener alternative

95%

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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About This Item

Linear Formula:
(C6H5CN)2PdCl2
CAS Number:
14220-64-5
Molecular Weight:
383.57
Beilstein:
3981730
EC Number:
238-085-3
MDL number:
MFCD00013123
UNSPSC Code:
12161600
PubChem Substance ID:
24853396
NACRES:
NA.22

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
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sustainability

Greener Alternative Product

mp

131 °C (lit.)

greener alternative category

Aligned,

SMILES string

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

InChI

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

InChI key

WXNOJTUTEXAZLD-UHFFFAOYSA-L

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General description

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


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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 and α-O-glycosidation.

Formal anti-Markovnikov hydroamination of terminal olefins

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
Synthesis, 803-803 (1992)
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
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.

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