[5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphane

• ChemBase ID: 68391
• Molecular Formular: C39H32OP2
• Molecular Mass: 578.618302
• Monoisotopic Mass: 578.1928389
• SMILES: C1(c2cccc(c2Oc2c(cccc12)P(c1ccccc1)c1ccccc1)P(c1ccccc1)c1ccccc1)(C)C
• Canonical SMILES: CC1(C)c2cccc(c2Oc2c1cccc2P(c1ccccc1)c1ccccc1)P(c1ccccc1)c1ccccc1
• InChI: 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
• InChIKey: CXNIUSPIQKWYAI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphane
• IUPAC Traditional name: xantphos
• Synonyms: 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene; Xantphos; 4,5-Bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene; 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene; Xantphos; 4,5-双(二苯基膦基)-9,9-二甲基呫吨; 4,5-双二苯基膦-9,9-二甲基氧杂蒽; 4,5-双(二苯基膦)-9,9-二甲基氧杂蒽

Database IDs

• CAS Number: 161265-03-8
• MDL Number: MFCD00233866
• PubChem SID: 162034122; 24874555
• PubChem CID: 636044
• Chemspider ID: 551930
• Wikipedia Title: Xantphos

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 10.3934
• LogD (pH = 7.4): 10.3934
• Log P: 10.3934
• Molar Refractivity: 186.6259 cm^3
• Polarizability: 69.32507 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: organic solvents
• Apperance: colorless solid
• Melting Point: 224 - 228°C; 224-228 °C(lit.); 224-228°C; 224-228°C
• Density: 1.34 g/mL
• Ligand For: Buchwald-Hartwig Cross Coupling Reaction; C-X Bond Formation; Hydroformylations; Miyaura Borylation Reaction; Stille Coupling; Suzuki-Miyaura Coupling

Safety Information

• Storage Warning: Harmful/Irritant; IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• Main Hazard: flammable
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95+%; 97%
• Empirical Formula (Hill Notation): C39H32OP2

DETAILS

Sigma Aldrich - 526460

Application
Ligand used in a synthesis of heterocycles by palladium-catalyzed C-N cross coupling of 3-bromothiophenes with 2-aminopyridines.1 Also used in a ruthenium-catalyzed alkylation of active methylene compounds with alcohols.2
Metal chelating ligand for catalysis.
Packaging
1, 5, 25 g in glass bottle