4,5,6,7-tetrahydro-1H-indol-4-one

• ChemBase ID: 90694
• Molecular Formular: C8H9NO
• Molecular Mass: 135.16316
• Monoisotopic Mass: 135.06841391
• SMILES: [nH]1c2c(cc1)C(=O)CCC2
• Canonical SMILES: O=C1CCCc2c1cc[nH]2
• InChI: InChI=1S/C8H9NO/c10-8-3-1-2-7-6(8)4-5-9-7/h4-5,9H,1-3H2
• InChIKey: KASJZXHXXNEULX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,5,6,7-tetrahydro-1H-indol-4-one
• IUPAC Traditional name: 1,5,6,7-tetrahydroindol-4-one
• Synonyms: 4-Oxo-4,5,6,7-tetrahydro-1H-indole; 1,5,6,7-Tetrahydro-4H-indol-4-one; 4,5,6,7-Tetrahydro-4-oxoindole; NSC 131681; 1,5,6,7-Tetrahydro-4H-indol-4-one; 6,7-dihydro-1H-indol-4(5H)-one; 1,5,6,7-四氢-4H-吲哚-4-酮

Database IDs

• CAS Number: 13754-86-4
• MDL Number: MFCD00075438
• PubChem SID: 162077448; 24861947
• PubChem CID: 280229

CALCULATED PROPERTIES

• Acid pKa: 14.340641
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.1251024
• LogD (pH = 7.4): 1.1251024
• Log P: 1.1251024
• Molar Refractivity: 39.117 cm^3
• Polarizability: 14.725782 Å^3
• Polar Surface Area: 32.86 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 188-190 °C(lit.); 190°C

Safety Information

• Storage Warning: Irritant/Light Sensitive/Store under Argon/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C8H9NO

DETAILS

Sigma Aldrich - 357839

Packaging
5 g in glass bottle
Application

• Reactant in synthesis of psammopemmin A as antitumor agent1
• Reactant in synthesis of a 1,3,4,5-tetrahydrobenzindole β-ketoesters and tricyclic tetrahydrobenzindoles via C-H insertion reactions2
• Reactant in preparation of tricyclic indole and dihydroindole derivatives as inhibitors of guanylate cyclase3
• Reactant in preparation of condensed pyrroloindoles via Pd-catalyzed intramolecular C-H bond functionalization of (halobenzyl)pyrroles4
• Reactant in enantioselective preparation of arylalkenyl indoles via asymmetric C-H insertion of rhodium carbenoids followed by Cope rearrangement-elimination5