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5-Methylindole-3-carboxylic acid methyl ester

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5-Methylindole-3-carboxylic acid methyl ester Basic information
Product Name:5-Methylindole-3-carboxylic acid methyl ester
Synonyms:RARECHEM AL BF 0707;Methyl 5-methylindole-3-carboxylate;5-METHYL-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER;METHYL 5-METHYL-1H-INDOLE-3-CARBOXYLATE;1H-Indole-3-carboxylicacid,5-Methyl-,Methylester;5-Methylindole-3-Carbocylic acid methyl ester;5-Methylindole-3-carboxylic acid methyl ester
CAS:227960-12-5
MF:C11H11NO2
MW:189.21
EINECS:607-884-2
Product Categories:Indole
Mol File:227960-12-5.mol
5-Methylindole-3-carboxylic acid methyl ester Structure
5-Methylindole-3-carboxylic acid methyl ester Chemical Properties
Boiling point 345.1±22.0 °C(Predicted)
density 1.212±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
pka15.59±0.30(Predicted)
AppearanceOff-white to light yellow Solid
CAS DataBase Reference227960-12-5(CAS DataBase Reference)
Safety Information
HS Code 2933998090
MSDS Information
5-Methylindole-3-carboxylic acid methyl ester Usage And Synthesis
Synthesis
Methanol

67-56-1

5-METHYL-1H-INDOLE-3-CARBOXYLIC ACID

10242-02-1

5-METHYLINDOLE-3-CARBOXYLIC ACID METHYL ESTER

227960-12-5

GENERAL PROCEDURE: Following the above procedure, the crude reaction mixture was diluted with methanol (MeOH) and cooled to 0 °C. Sulfoxide chloride (SOCl2, 36 μL, 0.5 mmol) was then slowly added and the reaction was stirred at room temperature for 3 hours. Upon completion of the reaction, additional methanol (MeOH) was added and the reaction mixture was heated to reflux for 6 hours. At the end of the reaction, the reaction was quenched with deionized water (H2O) and extracted with ethyl acetate (EtOAc, 3 times). All organic layers were combined and dried with anhydrous magnesium sulfate (MgSO4) and subsequently concentrated under reduced pressure. Finally, the crude product was purified by preparative thin layer chromatography (TLC, unfolding reagent ratio petroleum ether: ethyl acetate = 7:3) to afford the target compounds, methyl 5-methylindole-3-carboxylate (5a-b).

References[1] Heterocycles, 2015, vol. 90, # 2, p. 1196 - 1204
5-Methylindole-3-carboxylic acid methyl ester Preparation Products And Raw materials
Raw materials5-Methylindole-->5-Methyl-1H-indole-3-carboxylic acid-->N-(p-Tolyl)hydroxylamine-->Methanol-->Sodium Methoxide-->Methyl chloroformate-->4-Nitrotoluene-->2-Bromo-4-methylaniline-->Methyl propiolate-->Acryloyl chloride
Preparation Products9-Fluorenone
Tag:5-Methylindole-3-carboxylic acid methyl ester(227960-12-5) Related Product Information
5-Methyl-3-hydroxymethylindole 5-Methyl-1H-indole-3-carboxylic acid 5-Methylindole-3-carboxaldehyde 5-Methylindole-3-carboxylic acid methyl ester N-Methylindole-6-carboxylic acid methyl ester 2-Amino-5-trifluoromethyl-1H-indole-3-carboxylic acid ethyl ester 5-Methylindole Methyl indole-3-carboxylate 7-METHYLINDOLE-2-CARBOXYLIC ACID METHYL ESTER RARECHEM AL BI 0707