Description

3-Ethyl 4-Methyl 2-Aminothiophene-3,4-dicarboxylate (CAS No. 844502-63-2) is a high-purity synthetic organic compound with the molecular formula C₉H₁₁NO₄S. This thiophene derivative is characterized by its ethyl and methyl ester functionalities at the 3- and 4-positions, respectively, along with an amino group at the 2-position, making it a versatile intermediate for pharmaceutical and materials science research. Its IUPAC name, 3-O-ethyl 4-O-methyl 2-aminothiophene-3,4-dicarboxylate, reflects its precise structural configuration. This compound is supplied as a fine powder or crystalline solid with ≥95% purity (HPLC), ensuring consistency for synthetic applications. It is soluble in common organic solvents such as DMSO, methanol, and chloroform, but exhibits limited solubility in water. Store under inert conditions at 2-8°C to maintain stability. Suitable for use in heterocyclic synthesis, medicinal chemistry, and as a building block for functionalized thiophenes.

Properties

• CAS Number: 844502-63-2
• Complexity: 258
• IUPAC Name: O3-ethyl O4-methyl 2-aminothiophene-3,4-dicarboxylate
• InChI: InChI=1S/C9H11NO4S/c1-3-14-9(12)6-5(8(11)13-2)4-15-7(6)10/h4H,3,10H2,1-2H3
• InChI Key: JPILDOOERAALDC-UHFFFAOYSA-N
• Exact Mass: 229.04087901
• Molecular Formula: C9H11NO4S
• Molecular Weight: 229.26
• SMILES: CCOC(=O)C1=C(SC=C1C(=O)OC)N
• Topological: 107
• Monoisotopic Mass: 229.04087901
• Synonyms: 844502-63-2, 3-ETHYL 4-METHYL 2-AMINOTHIOPHENE-3,4-DICARBOXYLATE, DTXSID50679184, DTXCID60629933, 878-625-0, 3,4-Thiophenedicarboxylicacid, 2-amino-, 3-ethyl 4-methyl ester, 3-O-ethyl 4-O-methyl 2-aminothiophene-3,4-dicarboxylate, MFCD11977340, SCHEMBL5919196, AS-77142, E1418, D95412, A840788, O3-ethyl O4-methyl 2-azanylthiophene-3,4-dicarboxylate, 3-ETHYL4-METHYL2-AMINOTHIOPHENE-3,4-DICARBOXYLATE, 2-aminothiophene-3,4-dicarboxylic acid O3-ethyl ester O4-methyl ester

Application

3-Ethyl 4-Methyl 2-Aminothiophene-3,4-dicarboxylate serves as a key intermediate in the synthesis of bioactive thiophene derivatives for drug discovery, particularly in developing kinase inhibitors and antimicrobial agents. Its dual ester groups enable selective modifications for structure-activity relationship (SAR) studies. Researchers also utilize it in materials science to construct π-conjugated systems for organic electronics. The amino group facilitates further functionalization via amide coupling or Schiff base formation.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Precautionary Statements

• P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)

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