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Sigma-Aldrich

BrettPhos Pd G3

98%

Sinonimo/i:

[(2-Di-cyclohexylphosphino-3,6-dimethoxy-2′,4′,6′- triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′ -biphenyl)]palladium(II) methanesulfonate methanesulfonate

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250 MG
84,60 €
1 G
275,00 €
5 G
1.230,00 €
10 G
1.630,00 €

84,60 €


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Cambia visualizzazione
250 MG
84,60 €
1 G
275,00 €
5 G
1.230,00 €
10 G
1.630,00 €

About This Item

Formula empirica (notazione di Hill):
C48H66NO5PPdS
Numero CAS:
Peso molecolare:
906.50
Numero MDL:
Codice UNSPSC:
12352300
ID PubChem:
NACRES:
NA.22

84,60 €


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Livello qualitativo

Saggio

98%

Stato

solid

Caratteristiche

generation 3

Impiego in reazioni chimiche

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

Punto di fusione

150-193 °C (decomposition)

Gruppo funzionale

amine

Stringa SMILE

CS(=O)(O[Pd]c1c(c2c(N)cccc2)cccc1)=O.COc3c(P(C4CCCCC4)C5CCCCC5)c(c6c(C(C)C)cc(C(C)C)cc6C(C)C)c(OC)cc3

InChI

1S/C35H53O2P.C12H10N.CH4O3S.Pd/c1-23(2)26-21-29(24(3)4)33(30(22-26)25(5)6)34-31(36-7)19-20-32(37-8)35(34)38(27-15-11-9-12-16-27)28-17-13-10-14-18-28;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h19-25,27-28H,9-18H2,1-8H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1
PQYBJDCHLVJYSD-UHFFFAOYSA-M

Descrizione generale

BrettPhos Pd G3 is a third generation (G3) Buchwald precatalyst. It is air, moisture and thermally-stable and is highly soluble in a wide range of common organic solvents. It has long life in solutions. BrettPhos Pd G3 is an excellent reagent for Buchwald-Hartwig cross-coupling reaction. Some of its unique features include lower catalyst loadings, shorter reaction time, efficient formation of the active catalytic species and accurate control of ligand: palladium ratio.

Applicazioni

BrettPhos Pd G3 may be used for the C-N coupling reaction between monosubstituted ureas and 1,2 dihaloaromatic system to form benzimidazolones.[1][2]
It may be used in the synthesis of following compounds:
  • [Pd(cinnamyl)(BrettPhos)]OTf by reacting with [(cinnamyl)PdCl]2 and AgOTf.[3]
  • [Pd(crotyl)(BrettPhos)]OTf by reacting with [(crotyl)PdCl]2 and AgOTf.[3]
  • [Pd(allyl)(BrettPhos)]OTf by reacting with [(allyl)PdCl]2 and AgOTf.[3]
  • Pd(allyl)(BrettPhos)Clby reacting with [(allyl)PdCl]2.[3]
For small scale and high throughput uses, product is also available as ChemBeads (928321)

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


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I clienti hanno visto anche

Slide 1 of 7

1 of 7

Regioselective Synthesis of Benzimidazolones via Cascade C-N Coupling of Monosubstituted Ureas.
Ernst JB, et al.
Organic Letters, 16(14), 3844-3846 (2014)
Generating Active ?L-Pd (0)? via Neutral or Cationic Π-Allylpalladium Complexes Featuring Biaryl/Bipyrazolylphosphines: Synthetic, Mechanistic, and Structure-Activity Studies in Challenging Cross-Coupling Reactions.
DeAngelis AJ, et al.
The Journal of Organic Chemistry, 80(13), 6794-6813 (2015)
2-Aminobiphenyl Palladacycles: The ?Most Powerful? Precatalysts in C-C and C-Heteroatom Cross-Couplings.
Bruneau A, et al.
ACS Catalysis, 5(2), 1386-1396 (2015)

Articoli

Preformed catalysts in the kit are stable but become air-sensitive when activated; Schlenk technique aids scale-up.

All contents in the foil bag are weighed, plated, packed, and sealed in a glove box under nitrogen.

G3 and G4 Buchwald palladium precatalysts are the newest air, moisture, and thermally stable crossing-coupling complexes used in bond formation for their versatility and high reactivity.

Contenuto correlato

The Buchwald group has developed a series of highly active and versatile palladium precatalysts and biarylphosphine ligands used in cross-coupling reactions for the formation of C-C, C–N, C–O, C–F, C–CF3, and C–S bonds. The ligands are electron-rich, and highly tunable to provide catalyst systems with a diverse scope, high stability and reactivity. Furthermore, the new series of precatalysts are air-, moisture and thermally-stable and display good solubility in common organic solvents. The use of precatalysts ensures the efficient generation of the active catalytic species and allows one to accurately adjust the ligand:palladium ratio. The ligands, precatalysts and methodology developed in the Buchwald group are user friendly and have rendered previously difficult cross couplings reactions, much easier to achieve.

Explore reliable, premium grade catalysis materials for your pharma or industrial project. Specialty chemicals and formulations are available in bulk quantities and volumes from a few grams to multi-metric tons with complete documentation to simplify your leap from development to commercialization.

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

    1 risposta
    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 risposta
    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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