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701602

[1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II)

greener alternative

98%, powder

Synonym(s):

PdCl2(dtbpf)

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About This Item

Empirical Formula (Hill Notation):
C26H44Cl2FeP2Pd
CAS Number:
95408-45-0
Molecular Weight:
651.75
UNSPSC Code:
12161600
PubChem Substance ID:
329762308
NACRES:
NA.22
MDL number:
MFCD08064219
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Product Name

[1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II), 98%

Quality Level

200

assay

98%

form

powder

reaction suitability

core: palladium, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Cross Couplings, 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

203-208 °C

greener alternative category

, Aligned

storage temp.

−20°C

SMILES string

[Fe].Cl[Pd]Cl.CC(C)(C)P([C]1[CH][CH][CH][CH]1)C(C)(C)C.CC(C)(C)P([C]2[CH][CH][CH][CH]2)C(C)(C)C

InChI

1S/2C13H22P.2ClH.Fe.Pd/c2*1-12(2,3)14(13(4,5)6)11-9-7-8-10-11;;;;/h2*7-10H,1-6H3;2*1H;;/q;;;;;+2/p-2

InChI key

JQZFOBWXNREQLO-UHFFFAOYSA-L

General description

[1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dtbpf)) participates as catalyst in Suzuki and Heck reactions. It is a preformed catalyst synthesized by a group of researchers at Johnson Matthey′s Catalysis and Chiral Technologies. It is an active catalyst for various Pd catalyzed cross-coupling reactions.
[1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) is an air-stable, highly active and versatile catalyst. It is an efficient catalyst for cross-coupling reactions. It participates as catalyst in various coupling reactions of the fine chemicals and pharmaceutical chemicals. It is commonly employed as homogeneous catalyst in the Suzuki reactions.

PdCl2(dtbpf) is an air-stable cross-coupling catalyst used in the Suzuki coupling of various aryl chlorides.
We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Find details here.

Application

[1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dtbpf)) may be used as catalyst in the Suzuki cross-coupling reaction of various aromatic and heteroaromatic halides with methyliminodiacetic acid derivatives (MIDA boronates) at room temperature (in the absence of organic solvent). It may be employed as catalyst for the synthesis of chalcones, via cross-coupling reactions.
[1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) was used in the preparation of [PdCl2(bisphosphinometallocene)] complexes. These complexes are reported to be the catalyst precursors for the Buchwald-Hartwig reaction.
It is also employed as catalyst for greener Suzuki cross-coupling in TPGS-750-M.

On the Way Towards Greener Transition-Metal-Catalyzed Processes as Quantified by E Factors
Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Storage Class

11 - Combustible Solids

wgk

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
STBK5590
STBK3920
STBK2659
MKCP1808
STBJ8535

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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

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.

AdQPhos and Pd pre catalysts for alpha arylation reaction

Discover AdQPhos and its Pd pre-catalysts for selective α-arylation of diverse nucleophiles under mild aqueous conditions without hazardous solvents.

Bruce H Lipshutz et al.
Organic letters, 10(7), 1329-1332 (2008-03-14)
A nonionic amphiphile such as Triton X-100 or the vitamin E-based PTS, both of which form nanomicelles in water, promotes Heck cross-couplings of non-water-soluble partners at ambient temperatures. These are the first examples of Heck reactions conducted in water (as
An Effective Activation of Palladium Phosphine Complexes in Aqueous Phase Reactions of Hetero-Aromatic Boronic Acids with Aryl Halides.
Bumagin NA, et al.
Chemistry of Heterocyclic Compounds, 50(1), 19-25 (2011)
CRC International Symposium: Cross Coupling and Organometallics.
Colacot T.
Platinum Metals Rev., 52(3), 172-172 (2008)
View All Related Papers

Global Trade Item Number

SKUGTIN
701602-250MG04061833565100
701602-1G04061826700914
701602-50G04061833411605
701602-5G04061833330906