2-{[(2R)-6,7-dichloro-2-cyclopentyl-2-methyl-1-oxo-2,3-dihydro-1H-inden-5-yl]oxy}acetic acid

• ChemBase ID: 155341
• Molecular Formular: C17H18Cl2O4
• Molecular Mass: 357.22842
• Monoisotopic Mass: 356.05821442
• SMILES: C[C@@]1(Cc2cc(c(c(c2C1=O)Cl)Cl)OCC(=O)O)C1CCCC1
• Canonical SMILES: OC(=O)COc1cc2C[C@](C(=O)c2c(c1Cl)Cl)(C)C1CCCC1
• InChI: InChI=1S/C17H18Cl2O4/c1-17(10-4-2-3-5-10)7-9-6-11(23-8-12(20)21)14(18)15(19)13(9)16(17)22/h6,10H,2-5,7-8H2,1H3,(H,20,21)/t17-/m1/s1
• InChIKey: RNOJGTHBMJBOSP-QGZVFWFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(2R)-6,7-dichloro-2-cyclopentyl-2-methyl-1-oxo-2,3-dihydro-1H-inden-5-yl]oxy}acetic acid
• IUPAC Traditional name: {[(2R)-6,7-dichloro-2-cyclopentyl-2-methyl-1-oxo-3H-inden-5-yl]oxy}acetic acid
• Synonyms: Indanyloxyacetic acid 94; R(+)-Methylindazone; R(+)-[(6,7-Dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)-oxy]acetic acid; R(+)-IAA-94

Database IDs

• CAS Number: 54197-31-8
• PubChem SID: 24277844; 162249479
• PubChem CID: 6603874

CALCULATED PROPERTIES

• Acid pKa: 3.0556245
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.2093337
• LogD (pH = 7.4): 1.1533524
• Log P: 4.6209574
• Molar Refractivity: 87.508 cm^3
• Polarizability: 34.27812 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M NaOH: soluble2.8 mg/mL; dilute aqueous acid: insoluble; DMSO: >20 mg/mL; ethanol: soluble20 mg/mL; H2O: soluble0.2 mg/mL
• Apperance: white solid
• Optical Rotation: [α]22/D +36.4°, c = 0.86 in methanol(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: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H18Cl2O4

DETAILS

Sigma Aldrich - I117

Biochem/physiol Actions
Potent Cl- channel blocker.