718742

Sigma-Aldrich

2-(二环己基膦)3,6-二甲氧基-2′,4′,6′-三异丙基-1,1′-联苯

greener alternative

98%

别名:
BrettPhos
Empirical Formula (Hill Notation):
C35H53O2P
CAS号:
分子量:
536.77
MDL编号:
PubChem化学物质编号:
NACRES:
NA.22

质量水平

300

测定

98%

reaction suitability

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

reagent type: ligand
reaction type: Fluorinations

环保替代产品得分

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

环保替代产品特性

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

mp

187-195 °C

官能团

phosphine

环保替代产品分类

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

应用

BrettPhos是由 Buchwald 研究组开发的二烷基二芳基膦配体。与其他催化体系相比,它可以更有效地促进交叉偶联反应并显示出更高的反应性。
它可以用于:
  • 钯催化的芳基氯化物的三氟甲基化
  • Buwald-Hartwig氨基化
  • 通过Buchwald方法,合成4-芳基和烷基取代的 N6-烷基化-3,6-二氨基哒嗪

包装

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

特点和优势

  • 白色结晶固体
  • 空气和水分稳定
  • 热稳定
  • 高效
  • 广泛的官能团耐受性
  • 优异的选择性和转化率

storage_class_code

11 - Combustible Solids

WGK Germany

nwg

闪点(F)

Not applicable

闪点(C)

Not applicable

分析证书

原产地证书 (CofO)

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...
相关内容
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.
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