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PMC2010

APhos

Name: APhos
Brand: SIAL

≥98%, ISOM8^™

别名:

(4-(N,N-二甲氨基)苯基)二-叔丁基膦, A-^taPhos, [4-（二甲氨基）苯基]双（叔丁基）苯基

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关于此项目

经验公式（希尔记法）:

C₁₆H₂₈NP

化学文摘社编号:

932710-63-9

分子量:

265.37

NACRES:

NA.22

PubChem Substance ID:

24885360

UNSPSC Code:

12352128

MDL number:

MFCD09265102

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属性

product line

ISOM8^™

Quality Level

300

assay

(HPLC), ≥98%

form

solid

mol wt

265.37

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction, 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: catalyst, reagent type: ligand

mp

57-61 °C

application(s)

diagnostic assay manufacturing

functional group

phosphine

storage temp.

room temp

SMILES string

CN(C)c1ccc(cc1)P(C(C)(C)C)C(C)(C)C

InChI

1S/C16H28NP/c1-15(2,3)18(16(4,5)6)14-11-9-13(10-12-14)17(7)8/h9-12H,1-8H3

InChI key

IQTHEAQKKVAXGV-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.

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

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

Disclaimer

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.

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存储类别

11 - Combustible Solids

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Not applicable

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