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

• ChemBase ID: 138579
• Molecular Formular: C12H12FeO2
• Molecular Mass: 244.06748
• Monoisotopic Mass: 244.01866712
• SMILES: C1(=C[CH-]C=C1)CC(=O)O.[Fe+2].C1=C[CH-]C=C1
• Canonical SMILES: [CH-]1C=CC=C1.OC(=O)CC1=C[CH-]C=C1.[Fe+2]
• InChI: InChI=1S/C7H7O2.C5H5.Fe/c8-7(9)5-6-3-1-2-4-6;1-2-4-5-3-1;/h1-4H,5H2,(H,8,9);1-5H;/q2*-1;+2
• InChIKey: MOUVOWJUMAKBBM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: λ^2-iron(2+) ion 3-(carboxymethyl)cyclopenta-2,4-dien-1-ide cyclopenta-2,4-dien-1-ide
• IUPAC Traditional name: λ^2-iron(2+) ion 3-(carboxymethyl)cyclopenta-2,4-dien-1-ide cyclopentadienide
• Synonyms: FAA; NSC 128978; Ferroceneacetic acid; 二茂铁乙酸

Database IDs

• CAS Number: 1287-16-7
• MDL Number: MFCD00045464
• PubChem SID: 24860281; 162232832
• PubChem CID: 6477725

CALCULATED PROPERTIES

• Acid pKa: 4.6182656
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.067647874
• LogD (pH = 7.4): -1.8443387
• Log P: 1.8789
• Molar Refractivity: 33.0226 cm^3
• Polarizability: 12.910753 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 158-160 °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): C12H12FeO2

DETAILS

Sigma Aldrich - 335045

Packaging
500 mg in glass bottle
Application
Uses:
• Preparation of NADH oxidase-based NADH biosensors1
• Catalyst in hydroxylation and polymerization reactions2
• Reducing agent for reduction of Escherichia coli ribonucleotide reductase subunit R23
• Antitumor agent via generation of active oxygen species, which induce oxidative DNA damage in cancer cells4
• Catalyst for oxidation of ascorbic acid5