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PMC2006

2-二环己基磷-2′,4′,6′-三异丙基联苯

Name: 2-二环己基磷-2′,4′,6′-三异丙基联苯
Brand: SIAL

≥98%, ISOM8^™

别名:

XPhos

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关于此项目

经验公式（希尔记法）:

C₃₃H₄₉P

化学文摘社编号:

564483-18-7

分子量:

476.72

NACRES:

NA.22

PubChem Substance ID:

24882906

UNSPSC Code:

12352128

MDL number:

MFCD04117682

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属性

product line

ISOM8^™

Quality Level

300

assay

(HPLC), ≥98%

form

solid

mol wt

476.72

reaction suitability

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

greener alternative product score

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

greener alternative product characteristics

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

sustainability

Greener Alternative Product

mp

187-189 °C (Lit.), 187-190 °C (lit.)

application(s)

diagnostic assay manufacturing

functional group

phosphine

greener alternative category

Re-engineered

storage temp.

room temp

SMILES string

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

说明

General description

Welcome to our ISOM8^™ line of high-quality products available and able to scale for manufacturing. Within our ISOM8 team, we have expertise and documentation to support ISO 9001 industrial and non-GMP pharma production needs, as defined by our M-Clarity^™ Program.
Our portfolio of ISOM8 products and chemistries is ever evolving to support our valued Sigma-Aldrich^® customers′ requirements. Please navigate to our documents section to look at dossiers and other quality documentation for this product, provided with support of our Elevate Program.

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 “Use of Renewable Feedstocks”. Click here to view its DOZN scorecard.

Application

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。

Features and Benefits

Key Features & Applications

Buchwald Phosphine Ligands for Chemical Synthesis
Common applicationsBrettPhos, developed by the Buchwald group, is a highly effective dialkylbiaryl phosphine ligand that enhances transition metal-catalyzed reactions with unique steric and electronic properties.

Key Features:

Steric & Electronic Properties: Its bulky biaryl structure ensures stability, selectivity, and reduced side reactions, while the electron-deficient phosphine group boosts catalytic reactivity.
Metal Binding: Excellent for palladium and nickel-catalyzed processes like Suzuki and Buchwald-Hartwig reactions, stabilizing the metal center for improved efficiency.
Catalyst Stability: Enhances longevity and prevents degradation, delivering higher yields and cost-effectiveness under challenging conditions.
Versatility: Works across various solvents, temperatures, and reaction conditions, making it ideal for diverse synthetic processes.

Benefits:

Cross-Coupling Reactions: Promotes efficient carbon-carbon bond formation with minimal by-products in Suzuki-Miyaura, Heck, and Sonogashira reactions.
Diverse Substrate Compatibility: Performs well with challenging functional groups, enabling versatile synthetic pathways.
Enhanced Reaction Conditions: Allows for milder, eco-friendly reaction conditions.
Scalability: Suitable for both small-scale labs and large-scale industrial applications, ensuring consistent results.

Other Notes

Recent Studies and Innovations:

Recyclable Pd(acac)2/BrettPhos/PEG-1000 System for Suzuki-Miyaura Coupling: This study presents a sustainable catalytic system for nitroarenes, emphasizing its efficiency, recyclability, and greener approach to C–C bond formation. (Mingzhong Cai et al., 2024).
Pd-Catalyzed C–N Coupling via Buchwald–Hartwig Amination Using BrettPhos Ligand: This study demonstrates the scalability and efficiency of BrettPhos in palladium-catalyzed C–N bond formation, enabling selective coupling under mild conditions suitable for the synthesis of complex molecules on a larger scale. (Seb Caille et al., 2015).
Pd-Catalyzed Denitrative Cyanation of Nitroarenes with BrettPhos Ligand: This study highlights the denitrative cyanation of nitroarenes using aminoacetonitriles. The method efficiently converts nitroarenes into aryl nitriles, offering a halogen- and metal-waste-free catalytic process suitable for large-scale applications. (Junichiro Yamaguchi et al., 2024).

Incorporating BrettPhos into your synthetic strategies enhances efficiency, reliability, and innovation, offering robust support for research applications while ensuring seamless scalability for manufacturing.

Legal Information

用法以美国专利 6307087 和 6395916 为准。

ISOM8 is a trademark of Sigma-Aldrich Co. LLC

M-CLARITY is a trademark of Merck KGaA, Darmstadt, Germany

SIGMA-ALDRICH is a registered trademark of Merck KGaA, Darmstadt, Germany

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存储类别

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c