[2-(diphenylphosphanyl)ethyl]diphenylphosphane

• ChemBase ID: 112296
• Molecular Formular: C26H24P2
• Molecular Mass: 398.416282
• Monoisotopic Mass: 398.13532403
• SMILES: C(CP(c1ccccc1)c1ccccc1)P(c1ccccc1)c1ccccc1
• Canonical SMILES: c1ccc(cc1)P(c1ccccc1)CCP(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C26H24P2/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/h1-20H,21-22H2
• InChIKey: QFMZQPDHXULLKC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-(diphenylphosphanyl)ethyl]diphenylphosphane
• IUPAC Traditional name: diphos
• Synonyms: BIS(1,2-DIPHENYLPHOSPHINO)ETHANE; Ethylenebis(diphenylphosphine); 1,2-Bis(diphenylphosphino)ethane; [2-(diphenylphosphanyl)ethyl]diphenylphosphane; 1,2-Bis(diphenylphosphino)ethane; Diphos; Dppe; 1,2-Bis(diphenylphosphino)ethane; 1,2-二(二苯基膦基)乙烷; 1,2-双(二苯基膦)乙烷; 1,2-双(二苯基磷烷基)乙烷

Database IDs

• CAS Number: 1663-45-2
• EC Number: 216-769-2
• MDL Number: MFCD00003047
• Beilstein Number: 761261
• PubChem SID: 24846735; 24848891; 24863460; 162096917
• PubChem CID: 74267
• CHEBI ID: 30669
• CHEMBL: 68683
• Chemspider ID: 66873
• Wikipedia Title: 1,2-Bis(diphenylphosphino)ethane

CALCULATED PROPERTIES

• Rotatable Bonds: 7
• Lipinski's Rule of Five: false
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 6.8128
• LogD (pH = 7.4): 6.8128
• Log P: 6.8128
• Molar Refractivity: 121.8328 cm^3
• Polarizability: 48.36459 Å^3
• Polar Surface Area: 0.0 Å^2

PROPERTIES

Physical Property

• Melting Point: 137-142 °C; 137-142 °C(lit.); 138-143°C; 140 - 142°C; 140-142 °C
• Hydrophobicity(logP): 6.858
• Ligand For: Carbonylations; C-C Bond Formation; Cycloadditions; Decarboxylations; Diels-Alder Reaction; Heck Reaction; Negishi Coupling; Suzuki-Miyaura Coupling

Safety Information

• Storage Warning: Air Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P280G-P305+P351+P338
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥96.0% (CH); 95%; 97%; 97+%; 99%
• Grade: purum
• Linear Formula: (C6H5)2PCH2CH2P(C6H5)2

DETAILS

MP Biomedicals - 05223395

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 106496

Packaging
10, 50 g in glass bottle
Application
Used to obtain mixed-metal clusters.1

Sigma Aldrich - 376728

Application
Ligand for metal-catalyzed allylic alkylation; decarboxylation of allylic esters; 1,3-diene synthesis; cycloaddition reactions; carbonylation reactions.
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 14823

Application
Ligand for metal-catalyzed allylic alkylation; decarboxylation of allylic esters; 1,3-diene synthesis; cycloaddition reactions; carbonylation reactions.
Other Notes
Phosphine ligand for palladium(0) and mainly nickel(II) catalyzed reactions1,2,3

REFERENCES

• The catalyst prepared in situ with Sodium tetrachloropalladate(II) hydrate, 11886, catalyzes the carbonylation of allylic halides at atmospheric pressure: Chem. Lett., 1873 (1989):
  
• Useful replacement for Triphenylphosphine, L02502, in the Staudinger and Mitsunobu reactions, with the advantage of easier separation of the by-product bis(phosphine oxide) due to its higher polarity compared with triphenylphosphine oxide: Tetrahedron Lett., 39, 7787 (1998). Has also been used as an alternative to PPh₃ for the halodehydroxylation of alcohols, e.g. in combination with Hexachloroethane, L14297, alkyl chlorides are formed; the phosphine oxide by-product can readily be separated by filtration: Tetrahedron Lett., 42, 2459 (2001).
• Chelating phosphorus ligand.
• The complex with NiCl₂ catalyzes the coupling of haloaromatic compounds with Grignard reagents: J. Org. Chem.,49, 478 (1984).