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678740

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

solid

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
UNSPSC Code:
12161600
PubChem Substance ID:
24885453
NACRES:
NA.22
MDL number:
MFCD09265123
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Product Name

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

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. 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

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.
Application Guide for Palladium Catalyzed Cross-Coupling Reactions

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN0263
SHBL9656
SHBJ9778
SHBJ5765
SHBJ2034

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Protocols

Cross-Coupling Reactions in Water

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

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.

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
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

Global Trade Item Number

SKUGTIN
678740-5G04061832748641
678740-1G04061832748634
678740-50G04061833411544