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PMC2002

G Phos

greener alternative

≥98%, ISOM8™

Synonym(s):

GPhos, Dicyclohexyl[3-(1,1-dimethylethoxy)-6-methoxy-2′,6′-bis(1-methylethyl)[1,1′-biphenyl]-2-yl]phosphine

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About This Item

Empirical Formula (Hill Notation):
C35H53O2P
CAS Number:
2489243-29-8
Molecular Weight:
536.77
UNSPSC Code:
12352128
NACRES:
NA.22
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product line

ISOM8™

Quality Segment

300

assay

(HPLC), ≥98%

form

solid

mol wt

536.77

reaction suitability

reaction type: Cross Couplings, reagent type: catalyst, reagent type: ligand

greener alternative product score

old score: 16
new score: 13
Find out more about DOZN™ Scoring

greener alternative product characteristics

Designing Safer Chemicals
Safer Solvents and Auxiliaries
Design for Energy Efficiency
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

230-233 °C

application(s)

diagnostic assay manufacturing

functional group

phosphine

greener alternative category

Re-engineered

storage temp.

room temp

SMILES string

O(C1=CC=C(OC(C)(C)C)C(=C1C=2C(=CC=CC2C(C)C)C(C)C)P(C3CCCCC3)C4CCCCC4)C

InChI

InChI=1S/C35H53O2P/c1-24(2)28-20-15-21-29(25(3)4)32(28)33-30(36-8)22-23-31(37-35(5,6)7)34(33)38(26-16-11-9-12-17-26)27-18-13-10-14-19-27/h15,20-27H,9-14,16-19H2,1-8H3

InChI key

JKLUIDIKASJZCK-UHFFFAOYSA-N

General description

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 “Designing Safer Chemicals”, “Safer Solvents and Auxiliaries” and “Design for Energy Efficiency”. Click here to view its DOZN scorecard.
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


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:
  • <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

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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Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

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