• Chemical structure of RockPhos (di-tert-butyl(2′,4′,6′-triisopropyl-3-methoxy-6-methyl-[1,1′-biphenyl]-2-yl)phosphine), CAS 1262046-34-3, ≥98% — bulky electron-rich biaryl phosphine ligand for palladium-catalysed C–O bond formation, coupling primary and secondary alcohols with aryl and heteroaryl halides, including electron-rich substrates. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.
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NorrChemica™

RockPhos

CAS 1262046-34-3 ≥98%

RockPhos | CAS 1262046-34-3 | ≥98%

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Technical Specifications

CAS Number 1262046-34-3
EC / EINECS Number 805-149-2
MDL Number MFCD20922895
SMILES CC1=C(C(=C(C=C1)OC)P(C(C)(C)C)C(C)(C)C)C2=C(C=C(C=C2C(C)C)C(C)C)C(C)C
InChI 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
InChIKey CVLLAKCGAFNZHJ-UHFFFAOYSA-N
PubChem CID 56641709
Molecular Formula C₃₁H₄₉OP
Molecular Weight 468.69 g/mol
Melting Point 121 - 131 °C
Solubility Soluble in THF, 1,4-dioxane, toluene, dichloromethane and ethyl acetate; practically insoluble in water. Air-sensitive in solution — prepare in degassed solvents under inert atmosphere.
Purity ≥98%
Physical Form White to off-white crystalline solid
HS Code 2931.90
Shelf Life Retest period: 36 months from date of manufacture
Storage Conditions Store in a cool, dry place in a tightly sealed container, protected from air and moisture

Product Description & Scientific Applications

RockPhos is a bulky dialkylbiaryl phosphine developed alongside tBuBrettPhos and BrettPhos for the classes of carbon–heteroatom coupling that defeat the standard ligand set. What separates it from its neighbours is one position: the substituent at the 6-position of the biarylphosphine scaffold has a profound effect on catalytic activity, and RockPhos carries a methyl group there.

C–O coupling with alcohols. It underpins a general system for palladium-catalysed C–O cross-coupling of aryl halides with secondary as well as primary alcohols — the hard case, because β-hydride elimination competes with reductive elimination. Bromopyridine, bromopyrimidine and bromoquinoline all couple with n-butanol in good to excellent yields. The head-to-head figure is the one that matters: coupling 4-bromoquinoline with a secondary alcohol gave 88% isolated product, where the previously best system for secondary alcohols gave none. Independent surveys place it among the most effective ancillary ligands reported for these couplings, alongside AdBippyPhos and JosiPhos CyPF-tBu.

Weak nucleophiles and fluorination. Catalysts based on it promote rapid C–O coupling in the 2-fluoroethoxylation of bromochalcones, despite fluoroalcohols being weak nucleophiles, and in catalytic fluorination it shows a reactivity profile similar to tBuBrettPhos.

Where it underperforms. One study reports surprisingly low reactivities with this ligand. In chalcone alkoxylation, tBuXPhos gave more alkoxylated derivatives in shorter reaction time at similar yields.

Further reading: For phosphine-ligand selection, palladium sources and precatalysts, and Suzuki–Miyaura and Buchwald–Hartwig reagent choice, see NorrChemica's Lab Journal guide: Phosphine Ligands for Cross-Coupling.

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Safety Information

Hazard Class Not regulated for transport
Transport Category Not classified as dangerous goods for transport (ADR/IATA/IMDG)
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