[4-(diphenylphosphanyl)butyl]diphenylphosphane

• ChemBase ID: 70578
• Molecular Formular: C28H28P2
• Molecular Mass: 426.469442
• Monoisotopic Mass: 426.16662416
• SMILES: C(CCCP(c1ccccc1)c1ccccc1)P(c1ccccc1)c1ccccc1
• Canonical SMILES: C(CP(c1ccccc1)c1ccccc1)CCP(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C28H28P2/c1-5-15-25(16-6-1)29(26-17-7-2-8-18-26)23-13-14-24-30(27-19-9-3-10-20-27)28-21-11-4-12-22-28/h1-12,15-22H,13-14,23-24H2
• InChIKey: BCJVBDBJSMFBRW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [4-(diphenylphosphanyl)butyl]diphenylphosphane
• IUPAC Traditional name: [4-(diphenylphosphanyl)butyl]diphenylphosphane
• Synonyms: 1,4-Bis(diphenylphosphino)butane; [4-(diphenylphosphanyl)butyl]diphenylphosphane; 1,4-Butanediylbis[diphenylphosphine]; 1,4-Butylenebis(diphenylphosphine); Tetramethylenebis(diphenylphosphine); dppb; 1,4-Bis(diphenylphosphino)butane; 1,4-双(联苯基膦)丁烷; 1,4-双(二苯基膦)丁烷

Database IDs

• CAS Number: 7688-25-7
• EC Number: 231-698-7
• MDL Number: MFCD00003051
• Beilstein Number: 706446
• PubChem SID: 162036293; 24848876; 24855845
• PubChem CID: 82124

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 7.6054
• LogD (pH = 7.4): 7.6054
• Log P: 7.6054
• Molar Refractivity: 131.0348 cm^3
• Polarizability: 52.058743 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 132-136 °C(lit.); 132-136°C
• Hydrophobicity(logP): 7.916
• Ligand For: Alkylations; Heck Reaction; Isomerizations; Negishi Coupling; Sonogashira Coupling; Stille Coupling; Suzuki-Miyaura Coupling

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 36/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H315-H319-H413
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (TLC); 95%; 95+%; 98%
• Grade: purum
• Linear Formula: (C6H5)2P(CH2)4P(C6H5)2

DETAILS

MP Biomedicals - 05220505

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 261947

Packaging
5, 25 g in glass bottle
Application
Employed as a ligand in Pd(0)-catalyzed acylcyanation of arylacetylenes1 and deprotection of allyloxycarbamates.2

Sigma Aldrich - 14805

Other Notes
Diphosphine used in organometallic chemistry1,2,3,4,5

REFERENCES

• Chelating ligand.
• Component of a chiral Rh-based homogeneous hydrogenation catalyst: Org. Synth. Coll., 8, 16 (1993).
• The PdCl ₂ complex catalyzes the Suzuki coupling of heteroaryl chlorides with boronic acids with reported advantages over other catalysts: Tetrahedron Lett ., 32, 2273 (1991); Tetrahedron, 48, 8117 (1992).