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NorrChemica™
QPhos
CAS 312959-24-3
≥98%
QPhos | CAS 312959-24-3 | ≥98%
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Technical Specifications
| CAS Number | 312959-24-3 |
| EC / EINECS Number | 636-539-9 |
| MDL Number | MFCD03788940 |
| SMILES | P([C-]12C3=C4C5=C1[Fe+2]23451234C(C5C=CC=CC=5)5=C1(C1C=CC=CC=1)C2(C1C=CC=CC=1)=C3(C1C=CC=CC=1)[C-]45C1C=CC=CC=1)(C(C)(C)C)C(C)(C)C |
| InChI | InChI=1S/C35H25.C13H22P.Fe/c1-6-16-26(17-7-1)31-32(27-18-8-2-9-19-27)34(29-22-12-4-13-23-29)35(30-24-14-5-15-25-30)33(31)28-20-10-3-11-21-28;1-12(2,3)14(13(4,5)6)11-9-7-8-10-11;/h1-25H;7-10H,1-6H3;/q2*-1;+2 |
| InChIKey | BOBUBHOXRCYKLI-UHFFFAOYSA-N |
| PubChem CID | 24885299 |
| Molecular Formula | C₄₈H₄₇FeP |
| Molecular Weight | 710.72 g/mol |
| Melting Point | 220 °C(dec.) |
| Solubility | Insoluble in water, soluble in common organic solvents |
| Purity | ≥98% |
| Physical Form | Orange to orange brownish crystalline solid |
| HS Code | 2931.90 |
| Shelf Life | Retest period: 36 months from date of manufacture |
| Storage Conditions | Store refrigerated (2–8 °C) in a tightly sealed container under inert gas (N₂ or Ar), protected from light |
Product Description & Scientific Applications
QPhos (1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene) is a bulky, electron-rich ferrocenyl monophosphine, and unusually among ligands of that class it is described as air- and moisture-stable, stable in air even in solution.
Its five phenyl groups block facial binding of the lower ring to the metal, the coordination mode a biaryl ligand can adopt. In the comparison that reports this, it was three times more active than the biaryl ligand it was tested against.
Applications and Reactions
- Amination of aryl halides: a general ligand for palladium-catalysed C–N coupling, named across the literature for catalytic activity with aryl halides and particularly aryl chlorides. High monoaryl-to-biaryl product ratios are reported, where competing systems require an excess of the amine.
- Arylation of enolates: this is where the ligand has its own ground rather than a shared mention. Preformed Reformatsky reagents are arylated at room temperature with a catalyst from a palladium dibenzylideneacetone source and this ligand; zinc-amide enolates couple with aryl bromides at room temperature; a single-flask three-component coupling of ketone enolates reaches 85% at 2 mol% catalyst and 22 °C; and a Negishi variant couples aryl bromides with Reformatsky zinc enolates to give arylated esters and amides.
- Alkylboronic acid coupling: reported as the first general procedure for coupling aryl halides with terminal alkylboronic acids without recourse to toxic or expensive bases.
- A documented limit: in an indole synthesis from ammonia it was among six ligands giving no reaction.
Further Reading
Practical guidance on choosing a phosphine ligand for palladium- and nickel-catalysed cross-coupling in NorrChemica's Lab Journal: 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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