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Sigma-Aldrich

BrettPhos

greener alternative

98%

Synonyme(s) :

2-(Dicyclohexylphosphino)3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl

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100 MG
33.50 CHF
500 MG
123.00 CHF
1 G
210.00 CHF
5 G
745.00 CHF
25 G
3 710.00 CHF
50 G
3 960.00 CHF

33.50 CHF


Date d'expédition estimée le25 mars 2025


Devis pour commande en gros

Sélectionner une taille de conditionnement

Changer de vue
100 MG
33.50 CHF
500 MG
123.00 CHF
1 G
210.00 CHF
5 G
745.00 CHF
25 G
3 710.00 CHF
50 G
3 960.00 CHF

About This Item

Formule empirique (notation de Hill):
C35H53O2P
Numéro CAS:
Poids moléculaire :
536.77
Numéro MDL:
Code UNSPSC :
12352112
ID de substance PubChem :
Nomenclature NACRES :
NA.22

33.50 CHF


Date d'expédition estimée le25 mars 2025


Devis pour commande en gros

Niveau de qualité

Essai

98%

Forme

solid

Capacité de réaction

reaction type: Cross Couplings

Pertinence de la réaction

reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction

reagent type: ligand
reaction type: Fluorinations

Score du produit alternatif plus écologique

old score: 8
new score: 1
Find out more about DOZN™ Scoring

Caractéristiques du produit alternatif plus écologique

Waste Prevention
Atom Economy
Design for Energy Efficiency
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

Pf

187-195 °C

Groupe fonctionnel

phosphine

Autre catégorie plus écologique

Chaîne SMILES 

COc1c(P(C2CCCCC2)C3CCCCC3)c(c4c(C(C)C)cc(C(C)C)cc4C(C)C)c(OC)cc1

InChI

1S/C35H53O2P/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/h19-25,27-28H,9-18H2,1-8H3

Clé InChI

WDVGNXKCFBOKDF-UHFFFAOYSA-N

Description générale

We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Waste Prevention”, “Atom Economy” and “Design for Energy Efficiency”. Click here to view its DOZN scorecard.

Application

BrettPhos is a dialkylbiaryl phosphine ligand developed by the Buchwald group. It promotes cross-coupling reactions more efficiently and exhibits improved reactivity compared to other catalytic systems.
It can be used in:
  • palladium-catalyzed trifluoromethylation of aryl chlorides[1]
  • Buchwald-Hartwig amination[2]
  • synthesis of 4-aryl and alkyl substituted, N6-alkylated pyridazine-3,6-diamines via a Buchwald protocol[3]
For small scale and high throughput uses, product is also available as ChemBeads (928348)

Caractéristiques et avantages

  • White crystalline solid
  • Air- and moisture-stable
  • Thermally stable
  • Highly efficient
  • Wide functional group tolerance
  • Excellent selectivity and conversion

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

nwg

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Certificats d'analyse (COA)

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

T M Rangarajan et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 20(44), 14218-14225 (2014-09-23)
We report an unprecedented BrettPhos ligand supported Pd-catalyzed CO bond-forming reaction of activated aryl halides with primary fluoroalkyl alcohols. We demonstrate that the Phosphine ligand (BrettPhos) possesses the property of altering the mechanistic pathway of reductive elimination from nucleophile to
Multi-kilo delivery of AMG 925 featuring a Buchwald?Hartwig amination and processing with insoluble synthetic intermediates.
Affouard C, et al.
Organic Process Research & Development, 19(3), 476-485 (2015)
The palladium-catalyzed trifluoromethylation of aryl chlorides.
Cho EJ, et al.
Science, 328(5986), 1679-1681 (2010)
Facile synthesis of 4-aryl and alkyl substituted, N 6-alkylated pyridazine-3, 6-diamines.
Wlochal J & Bailey A.
Tetrahedron Letters, 56(48), 6791-6794 (2015)
David S Surry et al.
Angewandte Chemie (International ed. in English), 47(34), 6338-6361 (2008-07-30)
Palladium-catalyzed amination reactions of aryl halides have undergone rapid development in the last 12 years, largely driven by the implementation of new classes of ligands. Biaryl phosphanes have proven to provide especially active catalysts in this context. This Review discusses

Contenu apparenté

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.

Questions

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

    1 answer
    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 answer
    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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