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Merck
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文件

638064

Sigma-Aldrich

2-二环己基磷-2′,4′,6′-三异丙基联苯

greener alternative

98%

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别名:
XPhos
经验公式（希尔记法）:
C33H49P
CAS号:
564483-18-7
分子量:
476.72
MDL编号:
MFCD04117682
UNSPSC代码:
12352103
PubChem化学物质编号:
24882906
NACRES:
NA.22

质量水平

300

检测方案

98%

反应适用性

reaction type: Cross Couplings
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: C-C Bond Formation
reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Hiyama Coupling
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Sonogashira Coupling
reagent type: ligand
reaction type: Stille Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

环保替代产品得分

old score: 2
new score: 1
Find out more about DOZN™ Scoring

环保替代产品特性

Waste Prevention
Atom Economy
Use of Renewable Feedstocks
Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

187-190 °C (lit.)

官能团

phosphine

环保替代产品分类

, Re-engineered

SMILES字符串

CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C2=C(P(C3CCCCC3)C4CCCCC4)C=CC=C2

InChI

1S/C33H49P/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3

InChI key

UGOMMVLRQDMAQQ-UHFFFAOYSA-N

相关类别

一般描述

Xphos-[2-二环己基膦基-2′,4′,6′-三异丙基联苯]是一种由Buchwald集团开发的空气稳定的富电子联芳基单膦配体2，以增强在交叉偶联反应过程中提高钯催化的反应性。
我们竭诚为您带来满足绿色替代产品四大类别要求的替代产品。本品属于重新设计产品类别，在“防止废弃物”、“原子经济性””、“使用可再生原料”以及“节能设计”绿色化学原则方面取得了重大进步。 点击此处查看其DOZN记分卡。
我们致力于为您提供更环保的替代产品，以符合“绿色化学的12项原则”的一项或多项原则要求。该产品为增强型，提高了催化效率。点击此处以获取更多信息。

应用

TPGS-750-M 绿色 Sonogashira 偶联的首选配体。

对于小规模和高通量应用，可选用ChemBeads形式(928364)

朝着通过E因子评定的绿色过渡金属催化过程目标前进
XPhose可作为配体用于以下反应：
  • 通过钯催化的烷基砜和芳基卤之间的Negishi交叉偶联用于制备官能化的苄基砜。
  • 与预研磨的乙酸钯（II）一起作为芳基氯化物与三丁基芳基锡烷进行Stille交叉偶联形成相应的联芳基化合物的预催化剂。
  • 与氯化铂一起催化末端芳基烷基与硅烷的氢化硅烷化反应以形成官能化的β-(E)-乙烯基硅烷。
用于Pd催化的生成Vindoline的C-15类似物的铃木偶联反应中的配体。
将2-卤代苯胺直接环化成Pd催化的吲哚和色氨酸. 区域规整聚噻吩的合成。
用于TPGS-750-M中更为环保的优选Sonogashira偶联配体。
用于深入研究芳烃磺酸酯、芳基卤的钯催化胺化和酰胺化反应的配体。

法律信息

用法以美国专利 6307087 和 6395916 为准。
用途受美国专利7,223,879保护

相关产品

产品编号
说明
价格

918008

GPhos, ≥95%

储存分类代码

13 - Non Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

分析证书(COA)

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Xphos ligand and platinum catalysts: A versatile catalyst for the synthesis of functionalized ?-(E)-vinylsilanes from terminal alkynes.
Hamze A, et al.
Journal of Organometallic Chemistry, 693(16), 2789-2797 (2008)
Peter D Johnson et al.
The Journal of organic chemistry, 71(20), 7899-7902 (2006-09-26)
Described are general protocols for the rapid construction of various C-15-substituted analogues of vindoline using palladium-catalyzed cross-coupling reactions. The required bromo- and iodovindolines were prepared in high yield by the reaction of vindoline with N-bromosuccinimide or N-iodosuccinimide, respectively. The study
Tetrahedron Letters, 47, 5143-5143 (2006)
Yanxing Jia et al.
The Journal of organic chemistry, 71(20), 7826-7834 (2006-09-26)
One-pot synthesis of indoles by a palladium-catalyzed annulation of ortho-haloanilines and aldehydes has been developed. Coupling of ortho-iodoaniline with aldehyde is realized under mild ligandless conditions [Pd(OAc)2, DABCO, DMF, 85 degrees C], whereas X-Phos is found to be the ligand
Palladium-Catalyzed Stille Cross-Coupling Reaction of Aryl Chlorides using a Pre-Milled Palladium Acetate and XPhos Catalyst System.
Advanced Synthesis & Catalysis, 350(7-8), 957-961 (2008)
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商品

Palladium-catalyzed Cross-coupling Reactions

A variety of palladium-catalyzed cross-coupling reactions can be run under mild room temperature conditions in water with TPGS- 750-M, using a variety of commercially available palladium complexes and ligands.

Buchwald Phosphine Ligands

Buchwald Phosphine Ligands

Buchwald Phosphine Ligands

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

实验方案

Cross-Coupling Reactions in Water

TPGS-750-M surfactant enables various reactions in water at room temperature, enhancing efficiency and versatility in synthesis.

相关内容

Catalexis Catalyst Screening Platform

The Catalexis platform enhances catalysis by digitally optimizing catalyst selection to identify the most effective phosphine ligands for cross-coupling reactions.

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

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