[3-(diphenylphosphanyl)propyl]diphenylphosphane; dichloronickel

• ChemBase ID: 148053
• Molecular Formular: C27H26Cl2NiP2
• Molecular Mass: 542.042262
• Monoisotopic Mass: 540.02402235
• SMILES: c1ccc(cc1)P(CCCP(c1ccccc1)c1ccccc1)c1ccccc1.Cl[Ni]Cl
• Canonical SMILES: C(CP(c1ccccc1)c1ccccc1)CP(c1ccccc1)c1ccccc1.Cl[Ni]Cl
• InChI: InChI=1S/C27H26P2.2ClH.Ni/c1-5-14-24(15-6-1)28(25-16-7-2-8-17-25)22-13-23-29(26-18-9-3-10-19-26)27-20-11-4-12-21-27;;;/h1-12,14-21H,13,22-23H2;2*1H;/q;;;+2/p-2
• InChIKey: ZBQUMMFUJLOTQC-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: [3-(diphenylphosphanyl)propyl]diphenylphosphane; dichloronickel
• IUPAC Traditional name: [3-(diphenylphosphanyl)propyl]diphenylphosphane; nickel chloride
• Synonyms: (1,3-dppp)NiCl2; Ni(dppp)Cl2; 1,3-Bis(diphenylphosphino)propane nickel(II) chloride; [1,3-Bis(diphenylphosphino)propane]dichloronickel(II); 1,3-双(二苯基膦)丙烷氯化镍(II); [1,3-双(二苯基膦)丙烷]二氯化镍(II)

Database IDs

• CAS Number: 15629-92-2
• MDL Number: MFCD00015318
• PubChem SID: 162242232; 24860309
• PubChem CID: 2724937

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 7.1541
• LogD (pH = 7.4): 7.1541
• Log P: 7.1541
• Molar Refractivity: 126.3902 cm^3
• Polarizability: 50.2117 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 213 °C (dec.)(lit.)

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 49-36/37/38-42/43
• Safety Statements: 53-26-36/37/39-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H317-H319-H334-H335-H350
• GHS Precautionary statements: P201-P261-P280-P305 + P351 + P338-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Product Information

• Purity: ≥97.0% (C)
• Grade: purum
• Linear Formula: [(C6H5)2P(CH2)3P(C6H5)2]NiCl2

DETAILS

Sigma Aldrich - 335363

Packaging
5, 25 g in glass bottle
Application
Catalyst for:
• Synthesis of block-copolythiophenes1
• Suzuki-Miyaura cross-coupling reaction of aryl halides with arylboronic acids2
• Solid state metathesis polycondensation3
• Polymerization of poly(3-alkoxythiophene)s4
• Diastereoselective Nozaki-Hiyama-Kishi coupling reactions of C1-C19 fragment of macrolide antibiotic aplyronine A5
• Transfer condensation polymerization of conjugated polymers6

Sigma Aldrich - 14819

Other Notes
Catalyst used in the reaction of Grignard reagents with enol ethers to olefins. The diphosphine ligand minimizes reduction reactions by Grignard reagents with labile β-hydrogens7,8; Catalyst in reactions of Grignard reagents with dithioacetals and vinyl sulfides to olefins9,10
Application
Catalyst for:
• Synthesis of block-copolythiophenes1
• Suzuki-Miyaura cross-coupling reaction of aryl halides with arylboronic acids2
• Solid state metathesis polycondensation3
• Polymerization of poly(3-alkoxythiophene)s4
• Diastereoselective Nozaki-Hiyama-Kishi coupling reactions of C1-C19 fragment of macrolide antibiotic aplyronine A5
• Transfer condensation polymerization of conjugated polymers6