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95-20-5 - 2-Methylindole, 98+% - A10764 - Alfa Aesar

A10764 2-Methylindole, 98+%

CAS Number
95-20-5
Synonyms

Size Price ($) Quantity Availability
50g 37.90
250g 145.23
1000g 355.20
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2-Methylindole, 98+%

MDL
MFCD00005616
EINECS
202-398-3

Chemical Properties

Formula
C9H9N
Formula Weight
131.18
Melting point
56-60°
Boiling Point
272-273°
Flash Point
141°(285°F)
Density
1.07
Sensitivity
Light Sensitive
Solubility
Insoluble in water.

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.

Notes

Keep container tightly sealed. Store in cool, dry conditions in well sealed containers. Incompatible with oxidizing agents. It is sensitive to light.

Literature 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 Triethyl­silane, A10320, and TFA; e.g. with benzaldehyde, the 3-benzyl derivative is formed in 88% yield: Tetrahedron Lett., 34, 1529 (1993).

GHS Hazard and Precautionary Statements

Hazard Statements: H318

Causes serious eye damage.

Precautionary Statements: P280-P305+P351+P338-P310

Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician.

Other References

Beilstein
109781
Harmonized Tariff Code
2933.99
TSCA
Yes
RTECS
NM0345000

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