5-Nitro-benzo[b]thiophene-2-carboxylic acid methyl ester

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5-Nitro-benzo[b]thiophene-2-carboxylic acid methyl ester Basic information
Product Name:5-Nitro-benzo[b]thiophene-2-carboxylic acid methyl ester
Synonyms:METHYL 5-NITRO-1-BENZOTHIOPHENE-2-CARBOXYLATE;BUTTPARK 48\04-47;5-Nitro-1-benzothiophene-2-carboxylic acid methyl ester;5-Nitrothionaphthene-2-carboxylic acid methyl ester;Methyl 5-nitrobenzo[b]thiophene-2-carboxylate;5-nitrobenzo[b]thiophene-2-carboxylate;Benzo[b]thiophene-2-carboxylic acid, 5-nitro-, methyl ester;methyl 5-nitrobenzothiophene-2-carboxylate
CAS:20699-86-9
MF:C10H7NO4S
MW:237.23
EINECS:
Product Categories:
Mol File:20699-86-9.mol
5-Nitro-benzo[b]thiophene-2-carboxylic acid methyl ester Structure
5-Nitro-benzo[b]thiophene-2-carboxylic acid methyl ester Chemical Properties
Melting point 199-200 °C
Boiling point 393.2±22.0 °C(Predicted)
density 1.457±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
AppearanceLight yellow to yellow Solid
CAS DataBase Reference20699-86-9
Safety Information
HS Code 2934999090
MSDS Information
5-Nitro-benzo[b]thiophene-2-carboxylic acid methyl ester Usage And Synthesis
Synthesis
Methyl thioglycolate

2365-48-2

2-Chloro-5-nitrobenzaldehyde

6361-21-3

5-NITRO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER

20699-86-9

General procedure for the synthesis of methyl 5-nitrobenzo[b]thiophene-2-carboxylate from methyl mercaptoacetate and 2-chloro-5-nitrobenzaldehyde: To a solution of 2-chloro-5-nitrobenzaldehyde (3.7 g, 0.020 mol) in N,N-dimethylformamide (40 mL) was added methyl mercaptoacetate (1.82 mL, 0.020 mol), followed by potassium carbonate ( 3.3 g, 0.024 mol). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, water was added to the mixture and the suspension was filtered. The solid residue was washed with water to afford the target product methyl 5-nitrobenzo[b]thiophene-2-carboxylate as a yellow solid. Yield: 95%.

References[1] Synthetic Communications, 1991, vol. 21, # 7, p. 959 - 964
[2] Organic and Biomolecular Chemistry, 2015, vol. 13, # 24, p. 6814 - 6824
[3] Patent: WO2006/101454, 2006, A1. Location in patent: Page/Page column 45
[4] Patent: EP2876105, 2015, A1. Location in patent: Paragraph 0945; 0946
[5] Heterocycles, 2008, vol. 75, # 8, p. 1913 - 1929
5-Nitro-benzo[b]thiophene-2-carboxylic acid methyl ester Preparation Products And Raw materials
Raw materialsMethyl thioglycolate-->2-Fluoro-5-nitrobenzaldehyde-->2-Chloro-5-nitrobenzaldehyde-->Potassium carbonate-->N,N-Dimethylformamide
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