{2-[2-(diphenylphosphanyl)phenoxy]phenyl}diphenylphosphane

• ChemBase ID: 151021
• Molecular Formular: C36H28OP2
• Molecular Mass: 538.554442
• Monoisotopic Mass: 538.16153878
• SMILES: c1ccc(cc1)P(c1ccccc1)c1ccccc1Oc1ccccc1P(c1ccccc1)c1ccccc1
• Canonical SMILES: c1ccc(cc1)P(c1ccccc1Oc1ccccc1P(c1ccccc1)c1ccccc1)c1ccccc1
• InChI: InChI=1S/C36H28OP2/c1-5-17-29(18-6-1)38(30-19-7-2-8-20-30)35-27-15-13-25-33(35)37-34-26-14-16-28-36(34)39(31-21-9-3-10-22-31)32-23-11-4-12-24-32/h1-28H
• InChIKey: RYXZOQOZERSHHQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-[2-(diphenylphosphanyl)phenoxy]phenyl}diphenylphosphane
• IUPAC Traditional name: {2-[2-(diphenylphosphanyl)phenoxy]phenyl}diphenylphosphane
• Synonyms: DPEPhos; Bis[(2-diphenylphosphino)phenyl] ether; (Oxydi-2,1-phenylene)bis(diphenylphosphine); Bis[(2-diphenylphosphino)phenyl] ether; Bis[2-(diphenylphosphino)phenyl] ether; (Oxybis(2,1-phenylene))bis(diphenylphosphine); 双[(2-二苯膦基)苯基]醚; 双(2-二苯基磷苯基)醚

Database IDs

• CAS Number: 166330-10-5
• EC Number: 000-000-0
• MDL Number: MFCD00233863
• Beilstein Number: 7729718
• PubChem SID: 24873467; 162245180
• PubChem CID: 4285986

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 9.5956
• LogD (pH = 7.4): 9.5956
• Log P: 9.5956
• Molar Refractivity: 163.4286 cm^3
• Polarizability: 64.61491 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 178-181°C; 184-187 °C(lit.)
• Ligand For: Buchwald-Hartwig Cross Coupling Reaction; Heck Reaction; Hydroaminations; Negishi Coupling; Suzuki-Miyaura Coupling

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• 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%; 98%
• Linear Formula: O[C6H4P(C6H5)2]2

DETAILS

Sigma Aldrich - 510017

Packaging
25 g in glass bottle

REFERENCES

• Bidentate ligand, investigated in Rh-catalyzed regioselective hydroformylation of olefins: Organometallics, 14, 3081 (1995). Reported by Buchwald to be highly effective in promoting the Pd-catalyzed N-arylation of anilines: Tetrahedron Lett., 39, 5327 (1998).