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678740

Sigma-Aldrich

(AMPHOS)2PdCl2

Synonyme(s) :

Bis[4-[Bis(tert-butyl)phosphino]-N, N-Dimethylbenzenamide]dichloropalladium

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About This Item

Formule empirique (notation de Hill):
C32H56Cl2N2P2Pd
Numéro CAS:
887919-35-9
Poids moléculaire :
708.07
Numéro MDL:
MFCD09265123
Code UNSPSC :
12161600
ID de substance PubChem :
24885453
Nomenclature NACRES :
NA.22

Forme

solid

Pertinence de la réaction

core: palladium
reagent type: catalyst
reaction type: Cross Couplings

Capacité de réaction

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

Groupe fonctionnel

phosphine

Chaîne SMILES 

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

Clé InChI

DWOZNANUEDYIOF-UHFFFAOYSA-L

Description générale

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

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.
  • 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.
  • In the synthesis of indenones by Pd-catalyzed annulation of an ortho-halobenzyl alcohol with internal alkynes.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315 - H319 - H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Microwave assisted synthesis of phenanthridine derivatives via Suzuki coupling and condensation
Dende SK, et al.
Results in Chemistry, 3, 00149-00149 (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)
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)
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
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.

Protocoles

Cross-Coupling Reactions in Water

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

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