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Ethyl 2-amino-4-methylthiophene-3-carboxylate

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Ethyl 2-amino-4-methylthiophene-3-carboxylate Basic information
Application
Product Name:Ethyl 2-amino-4-methylthiophene-3-carboxylate
Synonyms:BUTTPARK 29\08-49;Ethyl 2-amino-4-methyl-3-thiophenecarboxylate;2-AMINO-4-METHYL-THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER;Ethyl 2-amino-4-methylthiophene-3-carboxylate, 98+%;Ethyl 2-amino-4-methylthiophene-3-carboxylate ,97%;2-Amino-3-(ethoxycarbonyl)-4-methylthiophene;2-aMino-5-ethyl-4-Methylthiophene-3-carboxylate;2-amino-4-methyl-3-thiophenecarboxylic acid ethyl ester
CAS:43088-42-2
MF:C8H11NO2S
MW:185.24
EINECS:674-825-5
Product Categories:Thiophene
Mol File:43088-42-2.mol
Ethyl 2-amino-4-methylthiophene-3-carboxylate Structure
Ethyl 2-amino-4-methylthiophene-3-carboxylate Chemical Properties
Melting point 80 °C
Boiling point 279℃
density 1.219
Fp 123℃
storage temp. Keep in dark place,Sealed in dry,Room Temperature
Water Solubility Soluble in water
form powder to crystal
pka0.24±0.10(Predicted)
color Light yellow to Yellow to Orange
BRN 1366073
InChIInChI=1S/C8H11NO2S/c1-3-11-8(10)6-5(2)4-12-7(6)9/h4H,3,9H2,1-2H3
InChIKeyILYCZKOBLRJJSW-UHFFFAOYSA-N
SMILESC1(N)SC=C(C)C=1C(OCC)=O
CAS DataBase Reference43088-42-2(CAS DataBase Reference)
Safety Information
Safety Statements 24/25
HazardClass IRRITANT
HS Code 29349990
MSDS Information
ProviderLanguage
ALFA English
Ethyl 2-amino-4-methylthiophene-3-carboxylate Usage And Synthesis
Application2-Amino-4-methyl-thiophene-3-carboxylic acid ethyl ester is an ester organic compound that can be used as a pharmaceutical intermediate.
Chemical PropertiesYellow solid
Synthesis
Ethyl cyanoacetate

105-56-6

Acetone

67-64-1

ETHYL 2-AMINO-4-METHYLTHIOPHENE-3-CARBOXYLATE

43088-42-2

GENERAL METHOD: Cyclohexanone (1.06 mL, 10 mmol), ethyl cyanoacetate (1.15 mL, 10 mmol), morpholine (0.90 mL, 10 mmol), and sulfur powder (0.32 g, 10 mmol) were dissolved in ethanol (10 mL), and the reaction was stirred and refluxed overnight. After completion of the reaction, the mixture was cooled to room temperature and the solvent was removed by distillation under reduced pressure. The resulting crude product was washed with cold ethanol, filtered through a sintered funnel and dried under vacuum. The dried crude product was dissolved in dichloromethane and washed with saturated saline. The organic layer was separated and concentrated under reduced pressure to afford the target compound ethyl 2-amino-4-methylthiophene-3-carboxylate (2a) in 73% yield (1.83 g).

References[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 13, p. 4418 - 4427
[2] European Journal of Medicinal Chemistry, 2014, vol. 86, p. 270 - 278
[3] Patent: CN107151251, 2017, A. Location in patent: Paragraph 0006; 0010
[4] Organic and Biomolecular Chemistry, 2014, vol. 12, # 24, p. 4233 - 4242
[5] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 95, p. 29 - 35
Ethyl 2-amino-4-methylthiophene-3-carboxylate Preparation Products And Raw materials
Raw materialsEthanol-->Sulfur-->Ethyl cyanoacetate-->Morpholine-->tert-Butyl acetoacetate-->Diethylamine-->Acetone
Preparation Products3-Thiophenecarboxylic acid, 2-amino-5-bromo-4-methyl-, ethyl ester-->4-Methylthiophene-3-carboxylic acid
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