23903-46-0

Basic information

• Product Name: 5-AMINO-4-CYANO-3-METHYL-THIOPHENE-2-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: ethyl 5-amino-4-cyano-3-methylthiophene-2-carboxylate(SALTDATA: FREE);5-amino-4-cyano-3-methyl-2-thiophenecarboxylic acid ethyl ester;Thiophene-2-carboxylic acid, 5-amino-4-cyano-3-methyl-, ethyl ester
• CAS NO: 23903-46-0
• Molecular Formula: C₉H₁₀N₂O₂S
• Molecular Weight: 210.26
• Mol File: 23903-46-0.mol
• Article Data: 12

Chemical Properties

• Melting Point: 151 °C
• Boiling Point: 386.6°Cat760mmHg
• Flash Point: 187.6°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 3.49E-06mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: 2-8°C
• PKA: -2.25±0.10(Predicted)
• CAS DataBase Reference: 5-AMINO-4-CYANO-3-METHYL-THIOPHENE-2-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-4-CYANO-3-METHYL-THIOPHENE-2-CARBOXYLIC ACID ETHYL ESTER(23903-46-0)
• EPA Substance Registry System: 5-AMINO-4-CYANO-3-METHYL-THIOPHENE-2-CARBOXYLIC ACID ETHYL ESTER(23903-46-0)

Safety Data

• Hazardous Substances Data: 23903-46-0(Hazardous Substances Data)

Usage

Chemical Properties

Grey solid

InChI:InChI=1/C9H10N2O2S/c1-3-13-9(12)7-5(2)6(4-10)8(11)14-7/h3,11H2,1-2H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 109-77-3 malononitrile 
• 105-50-0 diethyl 1,3-acetonedicarboxylate 

Downstream Products

• 443122-95-0 C₁₆H₁₃FN₂O₃S 
• 443122-22-3 C₁₆H₁₃ClN₂O₃S 
• 296898-19-6 C₁₇H₁₆N₂O₃S 
• 443910-39-2 C₁₇H₁₆N₂O₄S 
• 1429226-54-9 C₁₇H₁₃N₃O₃S 
• 443122-62-1 C₁₇H₁₆N₂O₄S 
• 896322-44-4 C₁₈H₁₆N₂O₅S 
• 443122-60-9 C₁₇H₁₆N₂O₃S 
• 443123-04-4 C₁₆H₁₃ClN₂O₃S 
• 1429226-55-0 C₂₁H₂₄N₄O₃S 
• 1429226-56-1 C₁₈H₁₇N₃O₄S 
• 1429226-57-2 C₁₈H₁₇N₃O₄S 
• 1429226-58-3 C₁₇H₁₇N₃O₅S₂ 
• 1429226-59-4 C₁₇H₁₇N₃O₅S₂ 

Relevant articles and documents

Microwave accelerated Gewald reaction: synthesis of 2-aminothiophenes

Microwave-promoted synthesis of 2-aminothiophenes by multicomponent reactions of a ketone with an active nitrile and elemental sulfur under KF-alumina catalysis is described.

Design, synthesis, neuroprotective, antibacterial activities and docking studies of novel thieno[2,3-d]pyrimidine-alkyne Mannich base and oxadiazole hybrids

A series of thieno[2,3-d]pyrimidine alkyne Mannich base derivatives (7a-e, 8a-e) and thieno[2,3-d]pyrimidine 1,3,4-oxadiazole derivatives (9a-e, 10a-e) have been synthesized and evaluated for their neuroprotective and neurotoxicity activities where 9a, 10d displayed good neuroprotection 10.6 and 11.88 μg/mL respectively against the H2O2 induced cell death at the EC50 values and 9b, 9d showed respective toxic effects on PC12 cells at CC50 86.12 and 94.16 μg/mL. Compounds 9a, 9e, 10a and 10b showed strong antibacterial activity against two gram positive (S. aureus, B. subtilis) and two gram-negative strains (E. coli, P. aeruginosa) and showed good binding affinities with C(30) carotenoid dehydrosqualene synthase, Gyrase A and LpxC. This is the first report for the demonstration of thieno[2,3-d] pyrimidine derivatives as promising neuroprotective agents against H2O2 induced neurotoxicity on PC12 cells.

Basic Ionic Liquid [bmIm]OH-Mediated Gewald Reaction as Green Protocol for the Synthesis of 2-Aminothiophenes

A simple, efficient, and environmental friendly procedure was developed based on the Gewald reaction for the synthesis of 2-aminothiophenes using a basic ionic liquid [bmIm]OH as both catalyst and solvent. Besides being a green protocol, the method offers advantages of successful synthesis of a variety of alkyl, aryl, alkoxy, and alkylamino-2-aminothiophenes in good yields.