λ2-iron(2+) ion 3-[cyclopenta-1,4-dien-3-id-1-yl(phenyl)phosphanyl]cyclopenta-2,4-dien-1-ide

• ChemBase ID: 151706
• Molecular Formular: C16H13FeP
• Molecular Mass: 292.093181
• Monoisotopic Mass: 292.01042455
• SMILES: c1ccc(cc1)P(C1=C[CH-]C=C1)C1=C[CH-]C=C1.[Fe+2]
• Canonical SMILES: c1ccc(cc1)P(C1=C[CH-]C=C1)C1=C[CH-]C=C1.[Fe+2]
• InChI: InChI=1S/C16H13P.Fe/c1-2-8-14(9-3-1)17(15-10-4-5-11-15)16-12-6-7-13-16;/h1-13H;/q-2;+2
• InChIKey: GQRVFMXNDVZWJD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: λ^2-iron(2+) ion 3-[cyclopenta-1,4-dien-3-id-1-yl(phenyl)phosphanyl]cyclopenta-2,4-dien-1-ide
• IUPAC Traditional name: λ^2-iron(2+) ion 3-[cyclopenta-1,4-dien-3-id-1-yl(phenyl)phosphanyl]cyclopenta-2,4-dien-1-ide
• Synonyms: 1,1′-(Ferrocenediyl)phenylphosphine; 1,1′-Bis(phenylphosphinidene)ferrocene; 1,1′-(二茂铁二基)苯膦; 1,1′-双(苯基亚膦基)二茂铁

Database IDs

• CAS Number: 72954-06-4
• MDL Number: MFCD04974069
• PubChem SID: 162245856; 24880349
• PubChem CID: 71311529

CALCULATED PROPERTIES

• Acid pKa: 13.257869
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.454476
• LogD (pH = 7.4): 2.4543993
• Log P: 5.5094
• Molar Refractivity: 72.9369 cm^3
• Polarizability: 29.112366 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 88-92 °C(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 97%
• Linear Formula: C5H4PC6H5C5H4Fe

DETAILS

Sigma Aldrich - 567159

Packaging
1 g in glass bottle
Application
Reactant for:
• Preparation of macrocyclic tridentate ferrocenylphosphine ligands1
• Preparation of phosphorus-bridged ferrocenophane with syn and anti conformations2
• Reaction with phenyllithium and chlorophosphine to give ferrocenediyl ligand and its rhodium complex catalyst for selective hydroformylation of alkenes3
• Ring-opening reactions via ring slippage4
• Preparation of palladium chloro (ferrocene-bridged)phosphine-phosphonite complex for catalysis of Heck reaction of iodobenzene with Me acrylate5