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Documenti

718742

Sigma-Aldrich

BrettPhos

greener alternative

98%

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C35H53O2P
Numero CAS:
1070663-78-3
Peso molecolare:
536.77
Numero MDL:
MFCD11973797
Codice UNSPSC:
12352112
ID PubChem:
329763602
NACRES:
NA.22

Livello qualitativo

300

Saggio

98%

Forma fisica

solid

Impiego in reazioni chimiche

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

Punteggio alternativa più verde

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

Caratteristiche più verdi

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

sustainability

Greener Alternative Product

Punto di fusione

187-195 °C

Gruppo funzionale

phosphine

Categoria alternativa più verde

, Re-engineered

Stringa SMILE

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
WDVGNXKCFBOKDF-UHFFFAOYSA-N

Categorie correlate

Descrizione generale

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.

Applicazioni

Buchwald Phosphine Ligands for chemical Synthesis
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)

Caratteristiche e vantaggi

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

nwg

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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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)
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)
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
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Contenuto correlato

Buchwald Group – Professor Product Portal

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.

Buchwald and non-Buchwald catalysts and ligands for pharma or industrial chemistry applications

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