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Merck

PMC2000

2-(ジシクロヘキシルホスフィノ)-3,6-ジメトキシ-2′,4′,6′-トリイソプロピル-1,1′-ビフェニル

greener alternative

≥98%, ISOM8™

別名:

BrettPhos

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この商品について

実験式（ヒル表記法）:
C35H53O2P
CAS番号:
1070663-78-3
分子量:
536.77
UNSPSC Code:
12352128
PubChem Substance ID:
329763602
NACRES:
NA.22
MDL number:
MFCD11973797

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SMILES string

COc1c(P(C2CCCCC2)C3CCCCC3)c(c4c(C(C)C)cc(C(C)C)cc4C(C)C)c(OC)cc1, COc1c(P(C2CCCCC2)C3CCCCC3)c(c4c(C(C)C)cc(C(C)C)cc4C(C)C)c(OC)cc1

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, 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, WDVGNXKCFBOKDF-UHFFFAOYSA-N

product line

ISOM8™

assay

(HPLC), ≥98%

form

solid

mol wt

536.77

reaction suitability

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

Quality Level

300

greener alternative product score

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

greener alternative product characteristics

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

sustainability

Greener Alternative Product

mp

191-194 °C (Lit.), 187-195 °C

application(s)

diagnostic assay manufacturing
life science and biopharma

functional group

phosphine

greener alternative category

Re-engineered

storage temp.

room temp

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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 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 “Design for Energy Efficiency”. Click here to view its DOZN scorecard

Application

Buchwald Phosphine Ligands for chemical Synthesis Common applications

BrettPhos, developed by the Buchwald group, is a highly effective dialkylbiaryl phosphine ligand that enhances transition metal-catalyzed reactions with unique steric and electronic properties.

Notable characteristics & key uses:

  • 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.
  • Cross-Coupling Reactions: Promotes efficient carbon-carbon bond formation with minimal by-products in Suzuki, 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.
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 scalabilityand efficiency of BrettPhos in palladium-catalyzed C–N bond formation, enablingselective coupling under mild conditions suitable for the synthesis of complexmolecules 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 amino acetonitriles. 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 ensurin gseamless scalability for manufacturing.
化学合成用のBuchwaldホスフィン配位子

Legal Information

ISOM8 is a trademark of Sigma-Aldrich Co. LLC

保管分類

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

適用法令

試験研究用途を考慮した関連法令を主に挙げております。化学物質以外については、一部の情報のみ提供しています。 製品を安全かつ合法的に使用することは、使用者の義務です。最新情報により修正される場合があります。WEBの反映には時間を要することがあるため、適宜SDSをご参照ください。

PMC2000-5G: + PMC2000-VAR: + PMC2000-1G: + PMC2000-10KG: + PMC2000-BULK: + PMC2000-1KG:

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