Skip to Content
Merck
CN

PMC2004

RockPhos

≥98%, ISOM8

Synonym(s):

RockPhos, Di-tert-butyl(2′,4′,6′-triisopropyl-3-methoxy-6-methyl-[1,1′-biphenyl]-2-yl)phosphine, 2-Di(tert-butyl)phosphino-2′,4′,6′-triisopropyl-3-methoxy-6-methylbiphenyl, Di-tert-butyl(2′,4′,6′-triisopropyl-3-methoxy-6-methyl-[1,1′-biphenyl]-2-yl)phosphine

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):
C31H49OP
CAS Number:
Molecular Weight:
468.69
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352128
MDL number:
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist


product line

ISOM8

Quality Level

assay

(HPLC), ≥98%

form

solid

mol wt

468.69

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: ligand

mp

121-131 °C

application(s)

diagnostic assay manufacturing

functional group

phosphine

storage temp.

room temp

SMILES string

CC1=C(C2=C(C(C)C)C=C(C(C)C)C=C2C(C)C)C(P(C(C)(C)C)C(C)(C)C)=C(OC)C=C1

InChI

1S/C31H49OP/c1-19(2)23-17-24(20(3)4)28(25(18-23)21(5)6)27-22(7)15-16-26(32-14)29(27)33(30(8,9)10)31(11,12)13/h15-21H,1-14H3

InChI key

CVLLAKCGAFNZHJ-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.

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

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.



Still not finding the right product?

Explore all of our products under RockPhos


Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

新产品

This item has



Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library



Global Trade Item Number

SKUGTIN
PMC2004-100G04065273598445
PMC2004-1G04065273598452
PMC2004-5G04065273598476
PMC2004-500G04065273598469