PMC2004

RockPhos

≥98%, ISOM8^™

• Synonym(e): 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
• Empirische Formel (Hill-System): C₃₁H₄₉OP
• CAS-Nummer: 1262046-34-3
• Molekulargewicht: 468.69
• NACRES: NA.22
• PubChem Substance ID: 329768254
• UNSPSC Code: 12352128
• MDL number: MFCD20922895
• eCl@ss: 32151101

Eigenschaften

• product line: ISOM8^™
• Quality Segment: 300
• 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

Beschreibung

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

Recent Studies and Innovations:

Mild and general C–O coupling of primary alcohols: Zhang et al. reported two complementary RockPhos-based catalyst systems providing mild and general conditions for the Pd-catalyzed C–O cross-coupling of primary alcohols with aryl and heteroaryl halides. The RockPhos Pd G3 precatalyst was specifically demonstrated for activated substrates, affording aryl ethers in high yields with excellent functional-group tolerance. (Zhang et al., 2018)

Improved process for secondary alcohol C–O cross-coupling: Zhang, Ruiz-Castillo, Schuppe, and Buchwald described an improved protocol for the Pd-catalyzed C–O cross-coupling of secondary alcohols with (hetero)aryl chlorides. The use of RockPhos as the ligand was key to achieving efficient coupling with only a 20% molar excess of alcohol, a significant advance over prior methods requiring stoichiometric excess and elevated temperatures. (Zhang et al., 2020)

• Buchwald Phosphine Ligands for chemical Synthesis
• Common applications

RockPhos is a sterically demanding dialkylbiaryl monophosphine ligand developed by the Buchwald group, designed to enable challenging palladium-catalyzed carbon–oxygen (C–O) cross-coupling reactions, as well as C–N and other bond-forming reactions with sterically demanding substrates.

Notable Characteristics & Key Uses

• High Steric Bulk and Electron Richness: RockPhos combines adi-tert-butylphosphino donor with a bulky tri-isopropyl/methoxy biarylbackbone, delivering a large cone angle that accelerates both oxidative addition of hindered aryl electrophiles and reductive elimination from palladium intermediates.
• Selectivity for C–O Bond Formation: RockPhos is particularlyoptimized for the intermolecular C–O coupling of aryl halides with primary andsecondary aliphatic alcohols, a transformation that is challenging with mostother phosphine ligands due to competing β-hydride elimination.
• Broad Substrate Scope: The ligand enables coupling across awide range of aryl and heteroaryl halides (chlorides, bromides, and iodides)with structurally diverse alcohol nucleophiles, including those bearingsensitive functional groups and fluoroalkyl substituents.
• Low Palladium Loading: High catalyst turnover allowsreactions to proceed at palladium loadings as low as 0.5 mol%, reducing metalwaste and simplifying downstream purification, which is critical forpharmaceutical applications.
• Aryl ether synthesis: RockPhos supports palladium inthe formation of C–O bonds between aryl halides and primary or secondaryaliphatic alcohols, providing efficient access to diaryl and alkyl aryl ethersthat are prevalent motifs in pharmaceuticals and agrochemicals.
• Coupling of primary alcohols under mild conditions: Using the RockPhos Pd G3 precatalyst, primary aliphatic alcohols coupleefficiently with diverse aryl and heteroaryl halides in good to excellentyields at moderate temperatures, making the method amenable to complex,multifunctional substrates.
• Improved C–O cross-coupling of secondary alcohols: RockPhos enables the challenging palladium-catalyzed C–O coupling of secondaryalcohols with (hetero)aryl chlorides using near-equimolar amounts of thealcohol partner, an advancement over earlier systems that required large excesses and higher temperatures.
• Synthesis of fluorinated alkyl aryl ethers: RockPhos-basedcatalysis provides access to fluorinated ether motifs via C–O cross-coupling offluoroalkyl alcohols with aryl halides, delivering building blocks of highrelevance for medicinal chemistry and drug discovery.

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

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable