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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/REAXYS Number:
3981730
EC Number:
238-085-3
MDL number:
MFCD00013123
UNSPSC Code:
12161600
PubChem Substance ID:
24853396
NACRES:
NA.22

Quality Level

100

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

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000315504
MKCV6486
MKCT1336
MKCR6298
0000222742

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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.
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)
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)

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