[2-(diphenylphosphanyl)ethenyl]diphenylphosphane

• ChemBase ID: 145329
• Molecular Formular: C26H22P2
• Molecular Mass: 396.400402
• Monoisotopic Mass: 396.11967396
• SMILES: c1ccc(cc1)P(/C=C/P(c1ccccc1)c1ccccc1)c1ccccc1
• Canonical SMILES: c1ccc(cc1)P(c1ccccc1)/C=C/P(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C26H22P2/c1-5-13-23(14-6-1)27(24-15-7-2-8-16-24)21-22-28(25-17-9-3-10-18-25)26-19-11-4-12-20-26/h1-22H
• InChIKey: NCKJIJSEWKIXAT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-(diphenylphosphanyl)ethenyl]diphenylphosphane; [(E)-2-(diphenylphosphanyl)ethenyl]diphenylphosphane
• IUPAC Traditional name: [2-(diphenylphosphanyl)ethenyl]diphenylphosphane; [(E)-2-(diphenylphosphanyl)ethenyl]diphenylphosphane
• Synonyms: cis-1,2-Bis(diphenylphosphino)ethene; cis-Vinylenebis(diphenylphosphine); cis-1,2-Bis(diphenylphosphino)ethylene; (E)-Vinylenebis[diphenylphosphine]; trans-1,2-Ethenediylbis(diphenylphosphine); NSC 132587; trans-1,2-Bis(diphenylphosphino)ethylene; 顺式-1,2-双(二苯基膦)乙烯; 反式-1,2-双(二苯基膦)乙烯; 反-1,2-双(二苯基膦基)乙烯

Database IDs

• CAS Number: 983-80-2; 983-81-3
• EC Number: 213-569-7; 213-570-2
• MDL Number: MFCD00063219; MFCD00003046
• Beilstein Number: 757793
• PubChem SID: 24859677; 162239535; 24857303
• PubChem CID: 2733288

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 6.9444
• LogD (pH = 7.4): 6.9444
• Log P: 6.9444
• Molar Refractivity: 121.286 cm^3
• Polarizability: 48.12584 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 122-124 °C(lit.); 126-130 °C(lit.); 126-130°C

Safety Information

• Storage Warning: Air Sensitive
• European Hazard Symbols: Irritant (Xi)
• UN Number: 3464
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-37; 26-37/39
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3464 6.1/PG 2

Product Information

• Purity: 97%; 98%
• Linear Formula: (C6H5)2PCH=CHP(C6H5)2

DETAILS

Sigma Aldrich - 327646

Packaging
1, 5 g in glass bottle

Sigma Aldrich - 287970

Packaging
1 g in glass bottle
Application
Catalyst for:
• Coupling of primary and secondary alkyl halides with aryl grignard reagents1
• Homogeneous hydrogenation of Carbon Dioxide mediated by Ruthenium2Reactant for:
• Preparation of cyclopalladated derivatives of benzylidene3
• Preparation of cyclopalladated complexes containing tridentate thiosemicarbazone ligands as antimalarial agents4
• Catalytic asymetric intramolecular hydroamination of alkynylamines5