526460

Xantphos

97%

• Synonym(s): 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene
• Empirical Formula (Hill Notation): C₃₉H₃₂OP₂
• CAS Number: 161265-03-8
• Molecular Weight: 578.62
• MDL number: MFCD00233866
• PubChem Substance ID: 24874555
• NACRES: NA.22

Properties

• Quality Level: 300
• Assay: 97%
• reaction suitability: reaction type: Cross Couplings; reagent type: ligand; reaction type: Buchwald-Hartwig Cross Coupling Reaction; reagent type: ligand; reaction type: C-X Bond Formation; 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 (lit.)
• functional group: phosphine
• 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

Description

General description

Xantphos is a bidentate ligand that is employed in various metal-catalyzed reactions, including cross-couplings, Buchwald-Hartwig cross-coupling reactions, C-X bond formation, hydroformylation, Miyaura borylation reaction, Stille coupling, Suzuki-Miyaura coupling, (hetero)arylation, amination, and amidation.

Application

Ligand used in a synthesis of heterocycles by palladium-catalyzed C-N cross coupling of 3-bromothiophenes with 2-aminopyridines. Also used in a ruthenium-catalyzed alkylation of active methylene compounds with alcohols.

Metal chelating ligand for catalysis.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315 - H319 - H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves