PMC2015
XantPhos
≥98%, ISOM8™
Synonym(s):
Xantphos, 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene, 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene
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About This Item
product line
ISOM8™
Quality Segment
assay
≥98%
form
solid
purified by
HPLC
reaction suitability
reagent type: ligand, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: C-X Bond Formation, reagent type: ligand
reaction type: Cross Couplings, reagent type: ligand
reaction type: Hydroformylations, reagent type: ligand
reaction type: Miyaura Borylation Reaction, reagent type: ligand
reaction type: Stille Coupling, reagent type: ligand
reaction type: Suzuki-Miyaura Coupling
mp
224-228 °C
application(s)
diagnostic assay manufacturing
life science and biopharma
functional group
phosphine
storage temp.
room temp
SMILES string
CC1(c2c(Oc3c1cccc3P(c4ccccc4)c5ccccc5)c(P(c6ccccc6)c7ccccc7)ccc2)C
InChI
1S/C39H32OP2/c1-39(2)33-25-15-27-35(41(29-17-7-3-8-18-29)30-19-9-4-10-20-30)37(33)40-38-34(39)26-16-28-36(38)42(31-21-11-5-12-22-31)32-23-13-6-14-24-32/h3-28H,1-2H3
InChI key
CXNIUSPIQKWYAI-UHFFFAOYSA-N
General description
Application
Notable Characteristics & Key Uses
- Chemical Structure: Xantphos features a rigid xanthene backbone providing a well-defined P-P distance. This structural rigidity allows it to coordinate metals in spanning or chelating modes, favoring both cis and trans complexes depending on reaction requirements.
- Large Natural Bite Angle: The wide bite angle of Xantphos is its most distinctive feature, promoting reductive elimination and enabling selective catalytic pathways - particularly beneficial in hydroformylation and cross-coupling.
- Bulky and Electron-Rich: The ligand′s steric profile and high electron density stabilize reactive metal complexes and enhance activity at the metal center.
- Versatile Metal Coordination: Xantphos effectively coordinates palladium, rhodium, nickel, platinum, and ruthenium, offering broad utility across multiple catalytic systems.
- Air and Moisture Stability: Xantphos is stable both as a solid and in solution, facilitating straightforward handling compared with more sensitive phosphine ligands.
- Amination and Amidation: Highly effective for Buchwald-Hartwig amination and amidation, Suzuki-Miyaura coupling, and Negishi coupling to form C-N, C-O, and C-C bonds, with particular utility in heterocycle synthesis.
- Carbonylation: Employed in palladium-catalyzed alkoxycarbonylation of alkenes for the efficient production of esters.
- C-S and C-O Bond Formation: Applied in cross-couplings to construct C-S bonds (e.g., glycosyl thiol synthesis) and C-O bonds (e.g., benzylic arylation).
- Hydrogenation: Utilized in ruthenium-catalyzed hydrogenation of carbon dioxide to formic acid or formate salts.
- Synthesis of Anilines: Xantphos was deployed in a low-loading palladium-catalyzed process for the production of 3-bromo-2,5-difluoroaniline. The cross-coupling of 1,3-dibromo-2,5-difluorobenzene with benzophenone imine afforded the desired imine intermediate in high yield (Christoper D et al., 2025).
- Superior Performance in Alkyl-Alkyl Cross-Coupling: Xantphos has been demonstrated to outperform alternative bisphosphine ligands in alkyl-alkyl cross-coupling due to its larger bite angle and structural rigidity, both of which are critical determinants of catalytic efficiency (Magali et al., 2025).
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Signal Word
Warning
Hazard Codes
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class
11 - Combustible Solids
Flash Point (°F)
Not applicable
Flash Point (°C)
Not applicable
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