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1-Ethyl-2-methylindole

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1-Ethyl-2-methylindole Basic information
Product Name:1-Ethyl-2-methylindole
Synonyms:N-ETHYL-2-METHYLINDOLE;1-ETHYL-2-METHYLINDOLE;1-ethyl-2-methyl-1H-indole;1-Ethyl-2-methylndole;1H-Indole, 1-ethyl-2-methyl-
CAS:40876-94-6
MF:C11H13N
MW:159.23
EINECS:255-121-3
Product Categories:Building Blocks;Heterocyclic Building Blocks;Indoles;Heterocycle-Indole series
Mol File:40876-94-6.mol
1-Ethyl-2-methylindole Structure
1-Ethyl-2-methylindole Chemical Properties
Boiling point 266-267 °C (lit.)
density 1.02 g/mL at 25 °C (lit.)
refractive index n20/D 1.587(lit.)
Fp >230 °F
storage temp. Store at room temperature
form powder to crystal
color White to Light yellow
InChI1S/C11H13N/c1-3-12-9(2)8-10-6-4-5-7-11(10)12/h4-8H,3H2,1-2H3
InChIKeyXMOWAIVXKJWQBJ-UHFFFAOYSA-N
SMILESCCn1c(C)cc2ccccc12
CAS DataBase Reference40876-94-6
EPA Substance Registry System1H-Indole, 1-ethyl-2-methyl- (40876-94-6)
Safety Information
WGK Germany 3
TSCA TSCA listed
HS Code 2933998090
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
SigmaAldrich English
1-Ethyl-2-methylindole Usage And Synthesis
Uses1-Ethyl-2-methylindole may be used in synthesis of hetrocyclic indole compounds.
Synthesis Reference(s)Synthesis, p. 617, 1979 DOI: 10.1055/s-1979-28783
Synthesis
2-Methylindole

95-20-5

Iodoethane

75-03-6

1-Ethyl-2-methylindole

40876-94-6

Example 1 Synthesis of JWH4511-ethyl-2-methylindole: To a reaction vial containing 0.20 g (1.52 mmol) of 2-methylindole was added 6 mL of a DMSO-dissolved solution of 0.38 g (6.89 mmol) of KOH, followed by 0.24 mL (3.04 mmol) of ethyl iodide. The reaction mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the reaction was quenched by the addition of 15 mL of water and extracted with ethyl acetate (2 x 15 mL). The organic phases were combined, washed sequentially with water (10 mL) and brine (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (eluent: ethyl ether/petroleum ether=0.5:9.5) to afford 0.20 g (83% yield) of the target compound N-ethyl-2-methylindole as a red oil.

References[1] Patent: WO2012/24670, 2012, A2. Location in patent: Page/Page column 43
[2] Synthesis, 1981, # 5, p. 389 - 390
[3] Organic Letters, 2017, vol. 19, # 17, p. 4680 - 4683
1-Ethyl-2-methylindole Preparation Products And Raw materials
Raw materials2-Methylindole-->Iodoethane-->Potassium hydroxide-->Dimethyl sulfoxide
Preparation ProductsASISCHEM W99822
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