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678740

Sigma-Aldrich

Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)

Synonym(s):

(A-taPhos)2PdCl2, Pd(amphos)Cl2

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About This Item

Empirical Formula (Hill Notation):
C32H56Cl2N2P2Pd
CAS Number:
887919-35-9
Molecular Weight:
708.07
MDL number:
MFCD09265123
UNSPSC Code:
12161600
PubChem Substance ID:
24885453
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
reaction type: Cross Couplings

functional group

phosphine

SMILES string

Cl[Pd]Cl.CN(c1ccc(P(C(C)(C)C)C(C)(C)C)cc1)C.CN(c2ccc(P(C(C)(C)C)C(C)(C)C)cc2)C

InChI

1S/2C16H28NP.2ClH.Pd/c2*1-15(2,3)18(16(4,5)6)14-11-9-13(10-12-14)17(7)8;;;/h2*9-12H,1-8H3;2*1H;/q;;;;+2/p-2

InChI key

DWOZNANUEDYIOF-UHFFFAOYSA-L

General description

Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine) dichloropalladium(II) is an organic compound with chemical formula C32H56Cl2N2P2Pd. [1] It is commonly used as a catalyst in the organic synthesis.[2]

For small scale and high throughput uses, product is also available as ChemBeads (927791)

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) is used as a catalyst:

  • In the enantioselective construction of indole-fused bicyclo[3.2.1]-octanes via an aminopalladition-triggered Heck-type reaction.[1]
  • In the synthesis of phenanthridine derivatives from ortho bromo N-tosylhydrazones and 2-aminophenylboronic ester via Suzuki cross-coupling reaction followed by intramolecular condensation reaction.[2]
  • In the synthesis of indenones by Pd-catalyzed annulation of an ortho-halobenzyl alcohol with internal alkynes.[3]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000411743
0000411743
0000411744
0000411744
0000282148

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Arkady Krasovskiy et al.
Journal of the American Chemical Society, 131(43), 15592-15593 (2009-10-16)
Mix in water, stir. That is all that is required in this new approach to sp(3)-sp(2) cross-couplings between an alkyl iodide and an aryl bromide, both potentially bearing functionality. They react under catalysis by Pd(0) in the presence of zinc
Microwave assisted synthesis of phenanthridine derivatives via Suzuki coupling and condensation
Dende SK, et al.
Results in Chemistry, 3, 00149-00149 (2021)
Enantioselective Synthesis of Indole-Fused Bicyclo [3.2. 1] octanes via Palladium (II)-Catalyzed Cascade Reaction
Wang G, et al.
Organic Letters, 23(3) (2021)
Palladium-catalyzed annulation of alkynes with ortho-halide-containing benzyl alcohols in aqueous medium
Feng J, et al.
The Journal of Organic Chemistry, 79(21), 10561-10567 (2014)
Anil S Guram et al.
Organic letters, 8(9), 1787-1789 (2006-04-21)
[reaction: see text] New air-stable PdCl(2){P(t)Bu(2)(p-R-Ph)}(2) (R = H, NMe(2), CF(3),) complexes represent simple, general, and efficient catalysts for the Suzuki-Miyaura cross-coupling reactions of aryl halides including five-membered heteroaryl halides and heteroatom-substituted six-membered heteroaryl chlorides with a diverse range of

Articles

An Introduction to A-Phos, its Applications and Advantages

Ligand used to prepare a palladium dichloride catalyst on treatment with PdCl2(COD). The catalyst effectively cross-couples aryl boronic acids with heteroaryl chlorides.

Palladium-catalyzed Cross-coupling Reactions

A variety of palladium-catalyzed cross-coupling reactions can be run under room temperature conditions in water with TPGS- 750-M, using a variety of commercially available palladium complexes and ligands.

Palladium-catalyzed Cross-coupling Reactions

A variety of palladium-catalyzed cross-coupling reactions can be run under room temperature conditions in water with TPGS- 750-M, using a variety of commercially available palladium complexes and ligands.

Palladium-catalyzed Cross-coupling Reactions

A variety of palladium-catalyzed cross-coupling reactions can be run under room temperature conditions in water with TPGS- 750-M, using a variety of commercially available palladium complexes and ligands.

See All

Protocols

Cross-Coupling Reactions in Water

TPGS-750-M surfactant enables various reactions in water at room temperature, enhancing efficiency and versatility in synthesis.

Cross-Coupling Reactions in Water

TPGS-750-M surfactant enables various reactions in water at room temperature, enhancing efficiency and versatility in synthesis.

Cross-Coupling Reactions in Water

TPGS-750-M surfactant enables various reactions in water at room temperature, enhancing efficiency and versatility in synthesis.

Cross-Coupling Reactions in Water

TPGS-750-M surfactant enables various reactions in water at room temperature, enhancing efficiency and versatility in synthesis.

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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