[1-(diphenylphosphanyl)ethenyl]diphenylphosphane

• ChemBase ID: 148905
• Molecular Formular: C26H22P2
• Molecular Mass: 396.400402
• Monoisotopic Mass: 396.11967396
• SMILES: C=C(P(c1ccccc1)c1ccccc1)P(c1ccccc1)c1ccccc1
• Canonical SMILES: C=C(P(c1ccccc1)c1ccccc1)P(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C26H22P2/c1-22(27(23-14-6-2-7-15-23)24-16-8-3-9-17-24)28(25-18-10-4-11-19-25)26-20-12-5-13-21-26/h2-21H,1H2
• InChIKey: GEGLBMPXRFOXTK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [1-(diphenylphosphanyl)ethenyl]diphenylphosphane
• IUPAC Traditional name: [1-(diphenylphosphanyl)ethenyl]diphenylphosphane
• Synonyms: VDPP; Vinylidenebis(diphenylphosphine); 1,1-Bis(diphenylphosphino)ethylene; 1,1-双(二苯基膦)乙烯

Database IDs

• CAS Number: 84494-89-3
• MDL Number: MFCD00191809
• PubChem SID: 162243076; 24863495
• PubChem CID: 4327892

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 7.5639
• LogD (pH = 7.4): 7.5639
• Log P: 7.5639
• Molar Refractivity: 130.4 cm^3
• Polarizability: 48.12358 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 110-111 °C(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%
• Linear Formula: [(C6H5)2P]2C=CH2

DETAILS

Sigma Aldrich - 377147

Packaging
1, 10 g in glass bottle
Application
Reactant for preparation of:
• Cyclometallated palladium diphosphane catalysts by Michael addition reactions1
• A-frame structures with palladacycles (chelating agent)2
• Functionalized bis-phosphine monoxide ligands catalyzed by chiral palladacycles3
• Tetranuclear palladacycles with bridging diphosphine ligands4
• Tetranuclear bromide-bridged Cu(I) complexes5
• Used as carbon-bridged diphosphine ligand in Cr-catalyzed ethylene tri- and tetramerization reactions6