XPhos
Empirical Formula (Hill Notation): | C33H49P |
CAS Number: | 564483-18-7 |
Molecular Weight: | 476.72 |
MDL number: | MFCD04117682 |
PubChem Substance ID: | 24882906 |
NACRES: | NA.22 |
Кат. номер |
638064-100G |
638064-12MG-KC |
638064-5G |
638064-25G |
638064-500G |
638064-1G |
XPhos [2-Dicyclohexylphosphino-2,4,6-triisopropylbiphenyl] is an air-stable electron-rich biaryl monophosphine ligand2 developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.
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Preferred ligand for greener Sonogashira coupling in TPGS-750-M.
XPhos may be used as a ligand in the following reactions:
- Preparation of functionalized benzylic sulfones via palladium-catalyzed Negishi cross-coupling between alkyl sulfones and aryl halides.
- Along with pre-milled palladium(II) acetate as a pre-catalyst for the Stille cross-coupling of aryl chlorides with tributylarylstannanes to form the corresponding biaryl compounds.
- Along with platinum chloride to catalyze the hydrosilylation of terminal arylalkynes with silanes to form functionalized -(E)-vinylsilanes.
Ligand used in a Pd-catalyzed Suzuki coupling leading to C-15 analogs of vindoline.
Direct annulation of 2-haloanilines to indoles and tryptophans catalyzed by Pd. Synthesis of regioregular polythiophenes.
Preferred ligand for greener Sonogashira coupling in TPGS-750-M.
On the Way Towards Greener Transition-Metal-Catalyzed Processes as Quantified by E Factors
Ligand for increased scope of Pd-catalyzed amination and amidation via arene sulfonates, aryl halides.
1, 5, 25, 100, 500 g in glass bottle
Usage subject to US Patent 7,223,879
Usage subject to US Patents 6307087 and 6395916.
Quality Level | 300 |
assay | 98% |
reaction suitability | reaction type: Cross Couplings, reagent type: ligand reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand reaction type: C-C Bond Formation, reagent type: ligand reaction type: Heck Reaction, reagent type: ligand reaction type: Hiyama Coupling, reagent type: ligand reaction type: Negishi Coupling, reagent type: ligand reaction type: Sonogashira Coupling, reagent type: ligand reaction type: Stille Coupling, reagent type: ligand reaction type: Suzuki-Miyaura Coupling |
greener alternative product score | old score: 2 new score: 1 Find out more about DOZN™ Scoring |
greener alternative product characteristics | Waste Prevention Atom Economy Use of Renewable Feedstocks Catalysis Learn more about the Principles of Green Chemistry. |
mp | 187-190 °C (lit.) |
functional group | phosphine |
greener alternative category | Re-engineered |
SMILES string | CC(C)c1cc(C(C)C)c(c(c1)C(C)C)-c2ccccc2P(C3CCCCC3)C4CCCCC4 |
InChI | 1S/C33H49P/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3 |
InChI key | UGOMMVLRQDMAQQ-UHFFFAOYSA-N |
Personal Protective Equipment | Eyeshields, Gloves, type N95 (US) |
RIDADR | NONH for all modes of transport |
WGK Germany | WGK 3 |
Flash Point(F) | Not applicable |
Flash Point(C) | Not applicable |