Search Thermo Fisher Scientific
Element Search
Structure Search
Thermo Scientific Chemicals
2-Methylindole, 98+%, Thermo Scientific Chemicals
Have Questions?
Change view
Catalog number A10764.18
also known as A10764-18
Price (USD)/ Each
52.80
-
Quantity:
50 g
Price (USD)/ Each
52.80
2-Methylindole, 98+%, Thermo Scientific Chemicals
Catalog numberA10764.18
Price (USD)/ Each
52.80
-
Chemical Identifiers
CAS95-20-5
IUPAC Name2-methyl-1H-indole
Molecular FormulaC9H9N
InChI KeyBHNHHSOHWZKFOX-UHFFFAOYSA-N
SMILESCC1=CC2=CC=CC=C2N1
View more
Specifications
Specification Sheet
Specification SheetFormCrystals or crystalline powder or granules or flakes
Assay (GC)≥98.0%
Appearance (Color)Yellow to red-purple to brown or purple
Identification (FTIR)Conforms
Melting Point (clear melt)55.0-61.0?C
2-Methylindole is used as a reactant for regioselective synthesis of oxopyrrolidine analogs via iodine-catalyzed Markovnikov addition reaction, Friedel-Crafts alkylation reactions, preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators, Michael addition reactions and in synthesis of cyclooxygenase-1 (COX-1)/cyclooxygenase-2 (COX-2) inhibitors.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
2-Methylindole is used as a reactant for regioselective synthesis of oxopyrrolidine analogs via iodine-catalyzed Markovnikov addition reaction, Friedel-Crafts alkylation reactions, preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators, Michael addition reactions and in synthesis of cyclooxygenase-1 (COX-1)/cyclooxygenase-2 (COX-2) inhibitors.
Solubility
Insoluble in water.
Notes
Keep container tightly sealed. Store in cool, dry conditions in well sealed containers. Incompatible with oxidizing agents. It is sensitive to light.
2-Methylindole is used as a reactant for regioselective synthesis of oxopyrrolidine analogs via iodine-catalyzed Markovnikov addition reaction, Friedel-Crafts alkylation reactions, preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators, Michael addition reactions and in synthesis of cyclooxygenase-1 (COX-1)/cyclooxygenase-2 (COX-2) inhibitors.
Solubility
Insoluble in water.
Notes
Keep container tightly sealed. Store in cool, dry conditions in well sealed containers. Incompatible with oxidizing agents. It is sensitive to light.
RUO – Research Use Only
General References:
- Ran Jiang.; Hai-Yan Xu.; Xiao-Ping Xu.; Xue-Qiang Chu.; Shun-Jun Ji. Direct alkylation of indoles and amines by tert-enamides: facile access to pharmaceutically active 2-oxo-1-pyrrolidine analogues. Organic & Biomolecular Chemistry. 2011, 9, (16), 5659-5669.
- Eduard Dolusic.; Pierre Larrieu.; Laurence Moineaux.; Vincent Stroobant.; Luc Pilotte.; Didier Colau.; Lionel Pochet.; Benoît Van den Eynde.; Bernard Masereel.; Johan Wouters.; Raphaël Frédérick. Tryptophan 2,3-dioxygenase (TDO) inhibitors. 3-(2-(pyridyl)ethenyl)indoles as potential anticancer immunomodulators. Journal of medicinal and pharmaceutical chemistry. 2011, 54 (15), 5320-5334.
- Can be dimetallated using the n-BuLi/KO-t-Bu system. Reaction with electrophiles (methyl iodide, benzophenone, t-butyl isocyanate) then occurs preferentially at the more reactive methyl position: J. Chem. Soc., Perkin 1, 179 (1990).
- An alternative approach to functionalization of the 2-methyl group involves low-temperature N-lithiation followed by reaction with dimethyl carbonate to give the 1-methoxycarbonyl derivative. NBS ɑ-bromination then allows nucleophilic substitution to give a variety of 2-substituted indoles: Synthesis, 743 (1992).
- Undergoes a mild, selective C-3 reductive alkylation in the presence of Triethyl silane, A10320, and TFA; e.g. with benzaldehyde, the 3-benzyl derivative is formed in 88% yield: Tetrahedron Lett., 34, 1529 (1993).