Cas no 80621-56-3 (Methyl 3-amino-4-nitrothiophene-2-carboxylate)

Methyl 3-amino-4-nitrothiophene-2-carboxylate is a heterocyclic compound featuring both amino and nitro functional groups on a thiophene backbone, esterified at the 2-position. This structure makes it a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and functional materials. The presence of reactive sites (amino and nitro groups) allows for further derivatization, enabling the construction of complex molecular architectures. Its stability under standard conditions and compatibility with common synthetic methodologies enhance its utility in multistep reactions. The compound is particularly valuable in medicinal chemistry for the development of thiophene-based bioactive molecules. Proper handling and storage are recommended due to its potential sensitivity to light and moisture.
Methyl 3-amino-4-nitrothiophene-2-carboxylate structure
80621-56-3 structure
Product Name:Methyl 3-amino-4-nitrothiophene-2-carboxylate
CAS No:80621-56-3
MF:C6H6N2O4S
MW:202.187839984894
CID:707737
PubChem ID:12940023
Update Time:2025-08-05

Methyl 3-amino-4-nitrothiophene-2-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Methyl 3-amino-4-nitrothiophene-2-carboxylate
    • 2-Thiophenecarboxylicacid, 3-amino-4-nitro-, methyl ester
    • DTXSID50513514
    • Methyl3-amino-4-nitrothiophene-2-carboxylate
    • 80621-56-3
    • G86895
    • DB-334797
    • 2-Thiophenecarboxylicacid,3-amino-4-nitro-,methylester(9CI)
    • Inchi: 1S/C6H6N2O4S/c1-12-6(9)5-4(7)3(2-13-5)8(10)11/h2H,7H2,1H3
    • InChI Key: DMEXFZJNWMIHRA-UHFFFAOYSA-N
    • SMILES: S1C=C(C(=C1C(=O)OC)N)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 202.00482785g/mol
  • Monoisotopic Mass: 202.00482785g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 3
  • Complexity: 229
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.5
  • Topological Polar Surface Area: 126?2

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Additional information on Methyl 3-amino-4-nitrothiophene-2-carboxylate

Methyl 3-amino-4-nitrothiophene-2-carboxylate (CAS No. 80621-56-3): A Key Intermediate in Modern Pharmaceutical Synthesis

Methyl 3-amino-4-nitrothiophene-2-carboxylate (CAS No. 80621-56-3) is a highly versatile and significant intermediate in the field of pharmaceutical synthesis. This compound, characterized by its thiophene core structure, has garnered considerable attention due to its utility in the development of various therapeutic agents. The presence of both amino and nitro functional groups on the thiophene ring endows it with unique reactivity, making it a valuable building block for synthetic chemists.

The< strong>Methyl 3-amino-4-nitrothiophene-2-carboxylate molecule exhibits a distinct chemical profile that facilitates its incorporation into complex molecular frameworks. The thiophene ring itself is a well-known scaffold in medicinal chemistry, frequently appearing in bioactive molecules across multiple therapeutic categories. Its aromatic nature and ability to engage in π-stacking interactions make it particularly useful in designing ligands for enzyme inhibition and receptor binding studies.

In recent years, the pharmaceutical industry has seen a surge in the exploration of heterocyclic compounds, with thiophenes being among the most studied scaffolds. The< strong>3-amino-4-nitrothiophene-2-carboxylate derivative stands out due to its dual functionality, which allows for diverse chemical transformations. These transformations can be tailored to introduce additional pharmacophores or to modify existing ones, thereby enabling the synthesis of novel drug candidates.

The< strong>CAS No. 80621-56-3 identifier ensures unambiguous recognition and traceability of this compound in both laboratory and industrial settings. This specificity is crucial for maintaining consistency in research protocols and ensuring compliance with regulatory standards. The compound’s stability under various storage conditions further enhances its practicality as an intermediate in multi-step synthetic pathways.

Recent advancements in synthetic methodologies have highlighted the importance of< strong>Methyl 3-amino-4-nitrothiophene-2-carboxylate in the development of targeted therapies. For instance, researchers have leveraged its structural features to design molecules with enhanced binding affinity to specific biological targets. This has been particularly relevant in the pursuit of treatments for neurological disorders, where precise molecular interactions are critical.

The< strong>nitro group on the thiophene ring plays a pivotal role in modulating the electronic properties of the molecule. This feature has been exploited to fine-tune pharmacokinetic profiles, such as metabolic stability and solubility, which are essential factors in drug development. Additionally, the< strong>amino group provides a handle for further derivatization, allowing chemists to introduce various substituents that can influence biological activity.

In academic research,< strong>Methyl 3-amino-4-nitrothiophene-2-carboxylate has been employed as a precursor in the synthesis of complex thiophene-based polymers and nanoparticles. These materials have potential applications in drug delivery systems, where controlled release mechanisms are desired. The compound’s ability to undergo polymerization reactions while maintaining its core structure makes it an attractive choice for such applications.

The pharmaceutical industry’s interest in< strong>CAS No. 80621-56-3-based compounds is also driven by their role as intermediates in producing anti-inflammatory and anticancer agents. The structural motifs present in< strong>Methyl 3-amino-4-nitrothiophene-2-carboxylate align well with known pharmacophores that exhibit therapeutic efficacy. By modifying this scaffold, scientists aim to discover new molecules with improved potency and reduced side effects.

The synthesis of< strong>Methyl 3-amino-4-nitrothiophene-2-carboxylate typically involves multi-step organic reactions that highlight modern synthetic techniques such as catalytic hydrogenation and palladium-catalyzed cross-coupling reactions. These methods ensure high yields and purity, which are imperative for pharmaceutical applications. The compound’s synthesis also underscores the importance of green chemistry principles, where minimal waste generation and energy efficiency are prioritized.

In conclusion, Methyl 3-amino-4-nitrothiophene-2-carboxylate (CAS No.< strong>80621-56-3) represents a cornerstone intermediate in contemporary pharmaceutical research and development. Its unique structural features and reactivity make it indispensable for constructing novel therapeutic agents across various disease indications. As research continues to uncover new applications for this compound, its significance is expected to grow further within the scientific community.

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