3-methyl-2,3-dihydro-1H-indol-2-one

• ChemBase ID: 152837
• Molecular Formular: C9H9NO
• Molecular Mass: 147.17386
• Monoisotopic Mass: 147.06841391
• SMILES: CC1c2ccccc2NC1=O
• Canonical SMILES: O=C1Nc2c(C1C)cccc2
• InChI: InChI=1S/C9H9NO/c1-6-7-4-2-3-5-8(7)10-9(6)11/h2-6H,1H3,(H,10,11)
• InChIKey: BBZCPUCZKLTAJQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methyl-2,3-dihydro-1H-indol-2-one
• IUPAC Traditional name: 3-methyloxindole
• Synonyms: 3-methyl-2,3-dihydro-1H-indol-2-one; 3-Methyl-2-indolinone; 3-Methyloxindole; 1,3-Dihydro-3-methyl-2H-indol-2-one; 3-Methyloxindole; 3-Methyl-2-oxindole; 3-Methyloxindole; 3-甲基吲哚酮; 3-甲基羟基吲哚

Database IDs

• CAS Number: 1504-06-9
• MDL Number: MFCD04037370
• PubChem SID: 162246980; 24872867
• PubChem CID: 150923

CALCULATED PROPERTIES

• Acid pKa: 13.252702
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.6150365
• LogD (pH = 7.4): 1.6150359
• Log P: 1.6150365
• Molar Refractivity: 44.1594 cm^3
• Polarizability: 16.314182 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 117-121 °C(lit.); 117-121°C; 120 - 122°C
• Hydrophobicity(logP): 1.226

Safety Information

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

Product Information

• Purity: 95%; 96%; 97%
• Empirical Formula (Hill Notation): C9H9NO

DETAILS

Sigma Aldrich - 493937

Packaging
5, 25 g in glass bottle
Application

• Reactant for enantioselective α-amination reactions1
• Reactant for aldol reaction with glyoxal derivatives2
• Reactant for amine thiourea catalyzed conjugate addition to α,β-unsaturated aldehydes3
• Reactant for O-acetylation reactions4
• Reactant for preparation of a disubstituted oxoindole by using rhodium-catalyzed cyclopropanation/ring-opening reactions5

Toronto Research Chemicals - M320660

3-Methylindole metabolite.

REFERENCES

• Skordos, K., et al.: Chem. Res. Toxicol., 11, 741 (1998)
• Lanza, D., et al.: Drug Metab. Disposition, 29, 950 (1998)
• Hoenicke, K., et al.: J. Agric. Food Chem., 50, 4303 (1998)