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493937

Sigma-Aldrich

3-Methyl-2-oxindole

96%

Synonym(s):

3-Methyloxindole

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About This Item

Empirical Formula (Hill Notation):
C9H9NO
CAS Number:
Molecular Weight:
147.17
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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

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

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ying Jin et al.
Chirality, 26(12), 801-805 (2014-07-22)
A series of cinchona alkaloid derivatives were used to catalyze the asymmetric anti-Mannich-type reaction of 3-methyl-2-oxindole with N-tosyl aryl aldimines. The resulting anti-3,3-disubstituted 2-oxindole products were obtained in good yields (up to 92%) with high diastereo- and enantioselectivities (anti/syn up
Metabolism and pneumotoxicity of 3-methyloxindole, indole-3-carbinol, and 3-methylindole in goats.
M J Potchoiba et al.
American journal of veterinary research, 43(8), 1418-1423 (1982-08-01)
Facile and Efficient Enantioselective Hydroxyamination Reaction: Synthesis of 3-Hydroxyamino-2-Oxindoles Using Nitrosoarenes.
Shen K, et al.
Angewandte Chemie (Weinheim an der Bergstrasse, Germany), 123(20), 4780-4784 (2011)
J Thornton-Manning et al.
The Journal of pharmacology and experimental therapeutics, 276(1), 21-29 (1996-01-01)
The toxicity of 3-methylindole (3 MI), a selective pneumotoxin, is dependent upon cytochrome P450-mediated bioactivation 3. Using vaccinia-expressed P450 enzymes, the metabolites of radiolabeled 3 MI produced by 14 individual P450s were identified and quantified by high performance liquid chromatography.
Jaroslav Matal et al.
Neuro endocrinology letters, 30 Suppl 1, 36-40 (2009-12-23)
To study the contribution of individual purified porcine CYP1A2, 2E1 and 2A19 enzymes to the biotransformation of skatole. Individual porcine and human enzymes (CYP1A2, 2E1 or 2A6/19) were used to study their potential involvement in skatole metabolism. Furthermore, the inhibition

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