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Merck

701602

Sigma-Aldrich

1,1′-Bis-(di-tert.-butylphosphino-)ferrocen-palladiumdichlorid

greener alternative

98%

Sinónimos:

PdCl2(dtbpf)

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About This Item

Fórmula empírica (notación de Hill):
C26H44Cl2FeP2Pd
Número de CAS:
Peso molecular:
651.75
Número MDL:
Código UNSPSC:
12161600
ID de la sustancia en PubChem:
NACRES:
NA.22
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Nivel de calidad

Ensayo

98%

Formulario

powder

idoneidad de la reacción

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

características de los productos alternativos más sostenibles

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

203-208 °C

categoría alternativa más sostenible

temp. de almacenamiento

−20°C

cadena SMILES

[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

Clave InChI

JQZFOBWXNREQLO-UHFFFAOYSA-L

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Descripción general

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.
[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]
[1,1′-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.[2] It is commonly employed as homogeneous catalyst in the Suzuki reactions.[3]

PdCl2(dtbpf) is an air-stable cross-coupling catalyst used in the Suzuki coupling of various aryl chlorides.[4]

Aplicación

[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).[5] It may be employed as catalyst for the synthesis of chalcones, via cross-coupling reactions.[6]
[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.[7]
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

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)


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Certificados de análisis (COA)

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Visite la Librería de documentos

The 2010 Nobel Prize in chemistry: palladium-catalysed cross-coupling.
Colacot TJ.
Platinum Metals Rev., 55(2), 84-90 (2011)
Natural and Synthetic Chalcones: Tools for the Study of Targets of Action-Insulin Secretagogue or Insulin Mimetic?
Nunes RJ, et al.
Stud. Nat. Prod. Chem., 39, 62-62 (2013)
A simple way of recycling of homogeneous catalyst in Suzuki reaction.
Manjunatha SG, et al.
Green Chemistry Letters and Reviews, 6(1), 77-87 (2013)
Synthesis and electrochemistry of late transition metal complexes containing 1, 1'-bis (dicyclohexylphosphino) ferrocene (dcpf). The X-ray structure of [PdCl 2 (dcpf)] and Buchwald-Hartwig catalysis using [PdCl2(bisphosphinometallocene)] precursors.
Hagopian LE, et al.
Journal of Organometallic Chemistry, 691(23), 4890-4900 (2006)
Gabriela A Grasa et al.
Organic letters, 9(26), 5489-5492 (2007-11-23)
alpha-Arylation of various ketones with aryl chlorides and bromides using the well-defined and air-stable (DtBPF)PdX2 (X = Cl, Br) catalysts gave 80-100% yield of the coupled products under relatively mild conditions at low catalyst loadings. The X-ray structure of (DtBPF)PdCl2

Artículos

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.

Protocolos

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

Preguntas

1–2 de 2 Preguntas  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 respuesta
    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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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 respuesta
    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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