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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:
1504-06-9
Molecular Weight:
147.17
MDL number:
MFCD04037370
UNSPSC Code:
12352100
PubChem Substance ID:
24872867
NACRES:
NA.22

Quality Level

100

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

Related Categories

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

493937-5G:
493937-VAR:
493937-BULK:
493937-25G:

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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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)
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
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
Takuma Sakurai et al.
Microorganisms, 7(9) (2019-09-14)
Recent studies have shown that metabolites produced by microbes can be considered as mediators of host-microbial interactions. In this study, we examined the production of tryptophan metabolites by Bifidobacterium strains found in the gastrointestinal tracts of humans and other animals.
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