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Merck

718742

Sigma-Aldrich

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

greener alternative

98%

Synonym(e):

BrettPhos

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About This Item

Empirische Formel (Hill-System):
C35H53O2P
CAS-Nummer:
Molekulargewicht:
536.77
MDL-Nummer:
UNSPSC-Code:
12352112
PubChem Substanz-ID:
NACRES:
NA.22

Qualitätsniveau

Assay

98%

Form

solid

Eignung der Reaktion

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

reagent type: ligand
reaction type: Fluorinations

Grünere Alternativprodukt-Bewertung

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

Grünere Alternativprodukt-Eigenschaften

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

mp (Schmelzpunkt)

187-195 °C

Funktionelle Gruppe

phosphine

Grünere Alternativprodukt-Kategorie

SMILES String

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

InChIKey

WDVGNXKCFBOKDF-UHFFFAOYSA-N

Allgemeine Beschreibung

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.

Anwendung

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
  • Buchwald-Hartwig amination
  • synthesis of 4-aryl and alkyl substituted, N6-alkylated pyridazine-3,6-diamines via a Buchwald protocol
For small scale and high throughput uses, product is also available as ChemBeads (928348)

Leistungsmerkmale und Vorteile

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

nwg

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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In der Dokumentenbibliothek finden Sie die Dokumentation zu den Produkten, die Sie kürzlich erworben haben.

Die Dokumentenbibliothek aufrufen

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)
The palladium-catalyzed trifluoromethylation of aryl chlorides.
Cho EJ, et al.
Science, 328(5986), 1679-1681 (2010)
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)
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
David S Surry et al.
Chemical science, 2(1), 27-50 (2011-01-01)
Dialkylbiaryl phosphines are a valuable class of ligand for Pd-catalyzed amination reactions and have been applied in a range of contexts. This review attempts to aid the reader in the selection of the best choice of reaction conditions and ligand

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