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493937 Sigma-Aldrich

3-Methyl-2-oxindole

96%

Synonym: 3-Methyloxindole

  • CAS Number 1504-06-9

  • Empirical Formula (Hill Notation) C9H9NO

  • Molecular Weight 147.17

  •  MDL number MFCD04037370

  •  PubChem Substance ID 24872867

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C7 to C9, Chemical Synthesis, Heterocyclic Building Blocks, Indoles More...
Quality Level   100
assay   96%
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 FeII 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

• 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

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

Packaging

5, 25 g in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

MSMLS Online Plate Map

Metabolite descriptors included with the software download upon purchase of the product include: Name, Parent CID, molecular formula, molecular weight, CAS, ChEBI, HMDB ID, PubChem Compound and Subst...
Keywords: Mass spectrometry, Metabolites

Peer-Reviewed Papers
15

References

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