493937

3-Methyl-2-oxindole

96%

• Synonym(s): 3-Methyloxindole
• Empirical Formula (Hill Notation): C₉H₉NO
• CAS Number: 1504-06-9
• Molecular Weight: 147.17
• MDL number: MFCD04037370
• UNSPSC Code: 12352100
• PubChem Substance ID: 24872867
• NACRES: NA.22

Properties

• Assay: 96%
• form: solid
• mp: 117-121 °C (lit.)
• SMILES string: CC1C(=O)Nc2ccccc12
• InChI: 1S/C9H9NO/c1-6-7-4-2-3-5-8(7)10-9(6)11/h2-6H,1H3,(H,10,11)
• InChI key: BBZCPUCZKLTAJQ-UHFFFAOYSA-N

Description

General description

3-Methyl-2-oxindole (MOI) is a 3-substituted-2-oxindole. It is reported to be formed during the oxidation of indole-3-acetic acid in the presence of Fe^II under aerobic conditions. MOI undergoes asymmetric anti-Mannich-type reaction with N-tosyl aryl aldimines in the presence of alkaloid cinchona derivatives to form anti-3,3-disubsituted 2-oxindole derivatives. It also undergoes asymmetric hydroxyamination with nitrosoarenes to form N-nitroso aldol products.

Application

3-Methyl-2-oxindole may be used in the preparation of 3-hydroxy-3-methyl-2-oxindole.

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

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves