PMC2015

XantPhos

≥98%, ISOM8^™

• Synonim(y): Xantphos, 9,9-Dimethyl-4,5-bis(diphenyl­phosphino)xanthene, 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene
• Wzór empiryczny (zapis Hilla): C₃₉H₃₂OP₂
• Numer CAS: 161265-03-8
• Masa cząsteczkowa: 578.62
• UNSPSC Code: 12352005
• MDL number: MFCD00233866
• NACRES: NA.21

Właściwości

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

Opis

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 quality documentation for this product, provided with support of our Elevate Program.

Application

Xantphos is a widely utilized bidentate bisphosphine ligand celebrated for its exceptionally large natural bite angle (~111 degrees). This distinctive geometric property makes Xantphos highly effective for palladium-catalyzed cross-coupling, rhodium-catalyzed hydroformylation, and the formation of C-N and C-O bonds, establishing it as one of the most versatile ligands in modern organometallic catalysis.

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.

Recent Studies and Innovations 

1. 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).
2. 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).

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

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Informacja o środkach bezpieczeństwa

• Piktogramy: GHS07
• Słowo ostrzegawcze: Warning
• Kody zagrożeń: H315,H319,H335
• Ostrzeżenia: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Narządy docelowe: Respiratory system
• Klasa składowania: 11 - Combustible Solids
• Temperatura zapłonu (°F): Not applicable
• Temperatura zapłonu (°C): Not applicable