λ2-iron(2+) ion 3-benzoylcyclopenta-2,4-dien-1-ide cyclopenta-2,4-dien-1-ide

• ChemBase ID: 131878
• Molecular Formular: C17H14FeO
• Molecular Mass: 290.13746
• Monoisotopic Mass: 290.03940257
• SMILES: c1ccc(cc1)C(=O)C1=C[CH-]C=C1.[CH-]1C=CC=C1.[Fe+2]
• Canonical SMILES: [CH-]1C=CC=C1.O=C(c1ccccc1)C1=C[CH-]C=C1.[Fe+2]
• InChI: InChI=1S/C12H9O.C5H5.Fe/c13-12(11-8-4-5-9-11)10-6-2-1-3-7-10;1-2-4-5-3-1;/h1-9H;1-5H;/q2*-1;+2
• InChIKey: PWUMGRPMAGSFJU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: λ^2-iron(2+) ion 3-benzoylcyclopenta-2,4-dien-1-ide cyclopenta-2,4-dien-1-ide
• IUPAC Traditional name: λ^2-iron(2+) ion 3-benzoylcyclopenta-2,4-dien-1-ide cyclopentadienide
• Synonyms: Benzoylferrocene; Ferrecenophenone; Ferrocenyl phenyl ketone; Ferrocenyl(phenyl)methanone; NSC 54800; (Benzoylcyclopentadienyl)cyclopentadienyliron; 苯甲酰基二茂铁; 苯甲酰二茂铁

Database IDs

• CAS Number: 1272-44-2
• EC Number: 215-054-2
• MDL Number: MFCD00001431
• PubChem SID: 162226155; 24861687
• PubChem CID: 16052452

CALCULATED PROPERTIES

• Acid pKa: 12.862139
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.688293
• LogD (pH = 7.4): 2.6882915
• Log P: 3.4694
• Molar Refractivity: 52.2905 cm^3
• Polarizability: 20.398958 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 105-107 °C(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98%
• Empirical Formula (Hill Notation): C17H14FeO

DETAILS

Sigma Aldrich - 349585

Packaging
5, 25 g in glass bottle
Application
Reactant for:
• Deprotonative metalation of ferrocenes1
• Oxidative chemistry2
• Reduction of ferrocenyl ketones3
• Polymerization of C-ferrocenyl-substituted phosphaalkene4Reactant for synthesis of:
• Planat chiral triferrocenylmethane derivative5
• Chiral ferrocenyl alcohols via asymmetric transfer hydrogenation6