718742

Sigma-Aldrich

BrettPhos

greener alternative

98%

Sinónimos:
2-(Dicyclohexylphosphino)3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl
Empirical Formula (Hill Notation):
C35H53O2P
Número de CAS:
Peso molecular:
536.77
Número MDL:
ID de la sustancia en PubChem:
NACRES:
NA.22

Nivel de calidad

300

ensayo

98%

reaction suitability

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

reagent type: ligand
reaction type: Fluorinations

puntuación de productos alternativos más sostenibles

old score: 8
new score: 1
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características de los productos alternativos más sostenibles

Waste Prevention
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Design for Energy Efficiency
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mp

187-195 °C

grupo funcional

phosphine

categoría alternativa más sostenible

Re-engineered

SMILES string

COc1ccc(OC)c(c1P(C2CCCCC2)C3CCCCC3)-c4c(cc(cc4C(C)C)C(C)C)C(C)C

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

Aplicación

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

Envase

1, 5, 25, 50 g in glass bottle
100, 500 mg in glass bottle

Características y beneficios

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

storage_class_code

11 - Combustible Solids

WGK Alemania

nwg

Punto de inflamabilidad F

Not applicable

Punto de inflamabilidad C

Not applicable

Certificado de Análisis

Certificado de origen

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...
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.
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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Más información
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.
Más información

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