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Sigma-Aldrich

Bis(triphenylphosphine)palladium(II) dichloride

Synonym(s):

Dichlorobis(triphenylphosphine)palladium(II), Palladium(II)bis(triphenylphosphine) dichloride, PdCl2(PPh3)2

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About This Item

Linear Formula:
[(C6H5)3P]2PdCl2
CAS Number:
13965-03-2
Molecular Weight:
701.90
Beilstein:
4935975
EC Number:
237-744-2
MDL number:
MFCD00009593
UNSPSC Code:
12161600
PubChem Substance ID:
24865821
NACRES:
NA.22
Pricing and availability is not currently available.

form

solid

Quality Level

200

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

SMILES string

Cl[Pd]Cl.c1(P(c2ccccc2)c3ccccc3)ccccc1.c4(P(c5ccccc5)c6ccccc6)ccccc4

InChI

1S/2C18H15P.2ClH.Pd/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;;/h2*1-15H;2*1H;/q;;;;+2/p-2

InChI key

YNHIGQDRGKUECZ-UHFFFAOYSA-L

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General description

Bis(triphenylphosphine)palladium(II) dichloride is an organometallic complex. It is an efficient cross-coupling catalyst for C-C coupling reaction, such as Negishi coupling, Suzuki coupling, Sonogashira coupling and Heck coupling reaction.[1][2] Detection of bis(triphenylphosphine)palladium(II) dichloride by electrospray ionization quadrupole ion trap mass spectrometry using different imidazolium salts as the charge carrier has been reported.[3] It is employed as catalyst for the Heck reaction medium.[4]

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Bis(triphenylphosphine)palladium(II) dichloride was employed in the following studies:
  • As model catalyst for the evaluation of functionalized silica′s for the adsorptive recovery of homogeneous catalysts, via its interaction with metal centre.[5]
  • As catalyst in the synthesis of diphenylacetylene.[6]
  • One-pot synthesis of furoquinolines, via Pd-catalyzed Sonogashira coupling followed by Cu(I) catalyzed ring closure.[7]
  • Catalyst for Sonogashira coupling of aryl alkynes to 2-bromothiazole and 2-bromothiophene.[1]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317,H413

Hazard Classifications

Aquatic Chronic 4 - Skin Sens. 1A

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW6025
0000187178
MKCS0989
MKCQ1179
MKCN5864

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Negishi, E.; Coperet, C., et al.
Journal of the American Chemical Society, 118, 5904-5904 (1996)
A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines.
Sonogashira K, et al.
Tetrahedron Letters, 16(50), 4467-4470 (1975)
Negishi, E.; Ay, M.; et al
Tetrahedron Letters, 34, 1437-1437 (1993)
Tetrahedron, 62, 9548-9548 (2006)
Tetrahedron Letters, 45, 4823-4826 (2004)
View All Related Papers

Questions

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  1. 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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  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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