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

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

• 60598-74-5 ethyl 4-amino-5-methylthieno[2,3-d]pyrimidine-6-carboxylate 
• 129811-87-6 ethyl 4-amino-5-cyano-3-methyl-6-phenylthieno<2,3-b>pyridine-2-carboxylate 
• 329059-62-3 ethyl 3-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]thieno[2,3-d]pyrimidine-2-carboxylate 
• 101667-97-4 5-Methyl-3,4-dihydrothieno<2,3-d>pyrimid-4-one-6-carboxylic acid 
• 421561-78-6 ethyl 5-methyl-4-morpholinothieno[2,3-d]pyrimidine-6-carboxylate 

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.

Synthesis and antitumor activity evaluation of some thienopyrimidine derivatives

Some novel thienopyrimidine derivatives were synthesized via the reaction of 5- methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-5-carbohydrazide with different carbonyl compounds such as anhydrides, acid chlorides, carbon disulfide, phenyl isothiocyanate, triethyl orthoformate, diethyl acetylene dicarboxylate, acetylacetone, pyrazole-4-carboxaldehyde, and isatin. Also, the reaction of this carbohydrazide derivative with sodium nitrite in the presence of hydrochloric acid to give the corresponding azide derivative was discussed. The latter azide derivative was reacted with different amines to give the corresponding diheteryl urea derivatives. The antitumor activity evaluation of some representative examples of the synthesized compounds was examined against HePG2 and MCF-7 cell lines. Some of the newly synthesized compounds showed significant activity.

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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.

Design and Synthesis of 4-Anilinothieno[2,3-d]pyrimidine-Based Compounds as Dual EGFR/HER-2 Inhibitors

Dual inhibition of the epidermal growth factor receptor (EGFR) and the human epidermal growth factor receptor 2 (HER-2) is an attractive cancer therapeutic approach. In this study, new series of 4-anilinothieno[2,3-d]pyrimidines were designed, synthesized, and tested as dual EGFR/HER-2 kinase inhibitors. Five compounds (8a, 8b, 8e–g) demonstrated low to submicromolar inhibition of both kinases with IC50 values of 1.2, 0.6, 0.3, 0.2, 0.4 μM and 8.2, 3.4, 1.3, 0.5, 2.7 μM for the EGFR and HER-2, respectively. Introduction of a 5,6-tetramethylene moiety into the thienopyrimidine core bearing a 4-(3-fluorobenzyloxy)-3-chloroaniline tail resulted in a favorable increase in both the EGFR and HER-2 inhibitory activities. Compound 8f (IC50 EGFR/HER-2: 0.2/0.5 μM) also exhibited significant cell growth inhibition on some specific NCI cell lines, especially ovarian, breast, non-small-cell lung cancer, and renal cancer cell lines.

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.

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