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Merck

718742

Sigma-Aldrich

BrettPhos

greener alternative

98%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C35H53O2P
Número de CAS:
Peso molecular:
536.77
MDL number:
UNSPSC Code:
12352112
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

form

solid

reaction suitability

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

reagent type: ligand
reaction type: Fluorinations

greener alternative product score

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

greener alternative product characteristics

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

sustainability

Greener Alternative Product

mp

187-195 °C

functional group

phosphine

greener alternative category

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

InChI key

WDVGNXKCFBOKDF-UHFFFAOYSA-N

General description

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
  • 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)

Features and Benefits

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

Storage Class

11 - Combustible Solids

wgk_germany

nwg

flash_point_f

Not applicable

flash_point_c

Not applicable


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Visite la Librería de documentos

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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