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Merck

PMC2003

Ru Phos

≥98%, ISOM8

Synonym(s):

RuPhos, 2-Dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl, Ru Phos

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About This Item

Empirical Formula (Hill Notation):
C30H43O2P
CAS Number:
Molecular Weight:
466.64
UNSPSC Code:
12352128
NACRES:
NA.22
PubChem Substance ID:
MDL number:
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InChI

1S/C30H43O2P/c1-22(2)31-27-19-13-20-28(32-23(3)4)30(27)26-18-11-12-21-29(26)33(24-14-7-5-8-15-24)25-16-9-6-10-17-25/h11-13,18-25H,5-10,14-17H2,1-4H3

SMILES string

CC(C)Oc1cccc(OC(C)C)c1-c2ccccc2P(C3CCCCC3)C4CCCCC4

InChI key

MXFYYFVVIIWKFE-UHFFFAOYSA-N

mp

123-126 °C

application(s)

diagnostic assay manufacturing

functional group

phosphine

storage temp.

room temp

product line

ISOM8

assay

(HPLC), ≥98%

form

solid

reaction suitability

reaction type: Arylations, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: C-X Bond Formation, reaction type: Cross Couplings, reaction type: Fluorinations

Quality Level

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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 dossiers and other quality documentation for this product, provided with support of our Elevate Program.

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Application

Buchwald Phosphine Ligands forchemical Synthesis


Common applications


RuPhos developed by the Buchwald group, RuPhos and its palladium precatalyst forms are notable for being air-stable, moisture-stable,and highly soluble, enabling efficient catalysis with lower catalyst loadings and shorter reaction times in organic synthesis.


Notable characteristics & key uses:

Steric & Electronic Properties: RuPhos′s biaryl structure with 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl configuration provides stability and selectivity. Its electron-rich phosphine and isopropoxy groups enhance catalytic reactivity and substrate compatibility.


Metal Binding: Excels in palladium and nickel-catalyzed processes including Suzuki-Miyaura coupling and Buchwald-Hartwig amination. Has a smaller Tolman cone angle than BrettPhos,donating less electron density to metals.


Catalyst Stability: RuPhos enhances catalyst longevity and prevents degradation, delivering higher yields even under demanding conditions with superior stability and solubility.


Versatility: Performs excellently across diverse solvents, temperatures, and reaction environments. Ideal forvaried applications, including Negishi cross-couplings of hindered aryl halides.


Cross-Coupling Reactions: RuPhos enablesefficient C-C, C-N, C-O, C-F, C-CF₃, and C-S bond formation with minimal by-products. Particularly effective with hindered substrates like cyclic secondary amines.


Precatalyst Integration: Incorporated into stable precatalysts like RuPhos Pd G3, offering enhanced handling and improved storage stability.


Enhanced Reaction Conditions: Facilitates milder, environmentally friendly reactions while maintaining high catalytic activity and selectivity.


Scalability: Suited for both laboratory research and industrial manufacturing, ensuring reproducible results across different operational scales.


Recent Studies and Innovations:




Steric Hindrance Effects: The study indicates that amines with large steric hindrance or halides with electron-withdrawing groups significantly reduce activation energy barriers in RuPhos-catalyzed reactions, enhancing overall catalytic efficiency and substrate scope. (Jiaqi Tian et al., 2020)

Catalyst-Transfer Polymerization (CTP): RuPhos excels in Suzuki−Miyaura catalyst-transfer polymerization (CTP), enabling precise synthesis of conjugated polymers with controlled molecular weights and narrow polydispersity. The ligand effectively facilitates polymerization of both electron-rich (donor) and electron-deficient (acceptor) monomers. (JaehoLee et al., 2021)

Legal Information

ISOM8 is a trademark of Sigma-Aldrich Co. LLC
M-CLARITY is a trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable


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