2-ジシクロヘキシルホスフィノ-2′,4′,6′-トリイソプロピルビフェニル
≥98%, ISOM8™
別名:
XPhos
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この商品について
実験式（ヒル表記法）:
C33H49P
CAS番号:
分子量:
476.72
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352128
MDL number:
product line
ISOM8™
Quality Level
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
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
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.
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
アレ-ンスルホナ-トやアリ-ルハライドのPd触媒によるアミノ化、アミド化反応を可能にする配位子です。
Features and Benefits
Key Features & Applications
Key Features:
Benefits:
- 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:
- <strong>Steric & Electronic Properties:</strong> Its bulky biaryl structure ensures stability, selectivity, and reduced side reactions, while the electron-deficient phosphine group boosts catalytic reactivity.
- <strong>Metal Binding:</strong> Excellent for palladium and nickel-catalyzed processes like Suzuki and Buchwald-Hartwig reactions, stabilizing the metal center for improved efficiency.
- <strong>Catalyst Stability:</strong> Enhances longevity and prevents degradation, delivering higher yields and cost-effectiveness under challenging conditions.
- <strong>Versatility:</strong> Works across various solvents, temperatures, and reaction conditions, making it ideal for diverse synthetic processes.
Benefits:
- <strong>Cross-Coupling Reactions:</strong> Promotes efficient carbon-carbon bond formation with minimal by-products in Suzuki-Miyaura, Heck, and Sonogashira reactions.
- <strong>Diverse Substrate Compatibility:</strong> Performs well with challenging functional groups, enabling versatile synthetic pathways.
- <strong>Enhanced Reaction Conditions:</strong> Allows for milder, eco-friendly reaction conditions.
- <strong>Scalability:</strong> Suitable for both small-scale labs and large-scale industrial applications, ensuring consistent results.
Other Notes
Recent Studies and Innovations:
Incorporating BrettPhos into your synthetic strategies enhances efficiency, reliability, and innovation, offering robust support for research applications while ensuring seamless scalability for manufacturing.
- <strong>Recyclable Pd(acac)<sub>2</sub>/BrettPhos/PEG-1000 System for Suzuki-Miyaura Coupling:</strong> 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).
- <strong>Pd-Catalyzed C–N Coupling via Buchwald–Hartwig Amination Using BrettPhos Ligand:</strong> 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).
- <strong>Pd-Catalyzed Denitrative Cyanation of Nitroarenes with BrettPhos Ligand:</strong> 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
米国特許番号第6,307,087号および第6,395,916号に従って使用してください。
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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保管分類
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable