Cas no 74440-05-4 ((Z)-2-(2-Aminothiazol-4-yl)-2-carboxymethoxyiminoacetic acid)

(Z)-2-(2-Aminothiazol-4-yl)-2-carboxymethoxyiminoacetic acid is a specialized organic compound featuring a thiazole ring with an amino substituent and a carboxymethoxyiminoacetic acid side chain. This structure imparts unique reactivity, making it valuable as an intermediate in pharmaceutical synthesis, particularly for β-lactam antibiotics. The presence of both amino and carboxyl functional groups enhances its versatility in coupling reactions, enabling precise modifications for targeted molecular design. Its stability under controlled conditions ensures consistent performance in synthetic applications. The compound’s well-defined stereochemistry (Z-configuration) further contributes to its utility in producing enantiomerically pure intermediates, supporting high-yield, selective transformations in advanced drug development.
(Z)-2-(2-Aminothiazol-4-yl)-2-carboxymethoxyiminoacetic acid structure
74440-05-4 structure
Product Name:(Z)-2-(2-Aminothiazol-4-yl)-2-carboxymethoxyiminoacetic acid
CAS No:74440-05-4
MF:C7H7N3O5S
MW:245.212579965591
CID:59591
PubChem ID:14193035
Update Time:2025-11-06

(Z)-2-(2-Aminothiazol-4-yl)-2-carboxymethoxyiminoacetic acid Chemical and Physical Properties

Names and Identifiers

    • (Z)-2-(2-Aminothiazol-4-yl)-2-carboxymethoxyiminoacetic acid
    • ( Z )-2-(2-AMINOTHIAZOL-4-YL)-2-CARBOXYMETHOXYIMINOACETIC ACID (ATCMA)
    • (Z)-2-(2-AMINOTHIAZOL-4-YL)-2-(TRITYLOXY)IMINOACETIC ACID
    • 4-Thiazoleaceticacid, 2-amino-a-[(carboxymethoxy)imino]-,(Z)-
    • 4-Thiazoleacetic acid,2-amino-a-[(carboxymethoxy)imino]-, (aZ)-
    • SCHEMBL16092898
    • 74440-05-4
    • SCHEMBL1023621
    • (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetic acid
    • AKOS015896636
    • Inchi: 1S/C7H7N3O5S/c8-7-9-3(2-16-7)5(6(13)14)10-15-1-4(11)12/h2H,1H2,(H2,8,9)(H,11,12)(H,13,14)/b10-5-
    • InChI Key: BTBQXVJMMALOJT-YHYXMXQVSA-N
    • SMILES: S1C(N)=NC(=C1)/C(/C(=O)O)=N/OCC(=O)O

Computed Properties

  • Exact Mass: 245.01100
  • Monoisotopic Mass: 245.011
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 9
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 5
  • Complexity: 321
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 1
  • Topological Polar Surface Area: 163A^2
  • XLogP3: 0.5

Experimental Properties

  • Density: 1.84
  • Boiling Point: 570.6°C at 760 mmHg
  • Flash Point: 298.9°C
  • Refractive Index: 1.725
  • PSA: 163.34000
  • LogP: 0.19640

(Z)-2-(2-Aminothiazol-4-yl)-2-carboxymethoxyiminoacetic acid Pricemore >>

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(Z)-2-(2-Aminothiazol-4-yl)-2-carboxymethoxyiminoacetic acid Related Literature

Additional information on (Z)-2-(2-Aminothiazol-4-yl)-2-carboxymethoxyiminoacetic acid

Comprehensive Overview of (Z)-2-(2-Aminothiazol-4-yl)-2-carboxymethoxyiminoacetic acid (CAS No. 74440-05-4)

(Z)-2-(2-Aminothiazol-4-yl)-2-carboxymethoxyiminoacetic acid (CAS No. 74440-05-4) is a specialized organic compound that has garnered significant attention in pharmaceutical and biochemical research. This compound, characterized by its unique aminothiazole and carboxymethoxyiminoacetic acid moieties, plays a pivotal role in the synthesis of advanced intermediates for antibiotics and other therapeutic agents. Its molecular structure, featuring a Z-configuration, is critical for its biological activity and stability, making it a subject of interest for researchers exploring novel drug formulations.

The compound's CAS No. 74440-05-4 is often searched in academic and industrial databases, reflecting its importance in the development of β-lactam antibiotics. Recent trends indicate a growing interest in its application for combating antibiotic-resistant bacteria, a pressing global health concern. Researchers are particularly intrigued by its potential to enhance the efficacy of existing antibiotics or serve as a building block for next-generation antimicrobial agents. This aligns with the rising demand for innovative solutions to address antimicrobial resistance (AMR), a topic frequently discussed in scientific and public health forums.

From a chemical perspective, (Z)-2-(2-Aminothiazol-4-yl)-2-carboxymethoxyiminoacetic acid exhibits remarkable reactivity due to its functional groups. The aminothiazole ring is known for its role in medicinal chemistry, often contributing to the bioactivity of compounds targeting bacterial enzymes. Meanwhile, the carboxymethoxyiminoacetic acid moiety provides versatility in synthetic pathways, enabling modifications that can optimize pharmacokinetic properties. These features make it a valuable candidate for drug discovery projects, particularly those focused on Gram-negative bacteria, which are notoriously difficult to treat.

In the context of green chemistry, there is increasing scrutiny on the environmental impact of chemical synthesis. (Z)-2-(2-Aminothiazol-4-yl)-2-carboxymethoxyiminoacetic acid has been studied for its potential to be produced via sustainable methods, such as catalytic processes or biocatalysis. This aligns with the broader industry shift toward eco-friendly manufacturing, a topic that resonates with both regulatory bodies and environmentally conscious consumers. Researchers are exploring ways to minimize waste and energy consumption during its production, addressing the dual challenges of cost-efficiency and sustainability.

The compound's relevance extends to patent literature and intellectual property discussions. Innovations involving CAS No. 74440-05-4 are frequently protected by patents, highlighting its commercial value. Companies specializing in fine chemicals and pharmaceutical intermediates often seek proprietary methods to synthesize or derivatize this compound, underscoring its strategic importance in the competitive landscape of drug development. This has led to a surge in publications and patents exploring its synthetic routes and applications.

Another area of interest is the compound's role in combinatorial chemistry and high-throughput screening. Its structural features make it a promising scaffold for generating diverse libraries of derivatives, which can be screened for various biological activities. This approach is particularly valuable in the era of precision medicine, where tailored therapies are increasingly sought after. By leveraging the versatility of (Z)-2-(2-Aminothiazol-4-yl)-2-carboxymethoxyiminoacetic acid, researchers can accelerate the discovery of compounds with optimized efficacy and safety profiles.

In summary, (Z)-2-(2-Aminothiazol-4-yl)-2-carboxymethoxyiminoacetic acid (CAS No. 74440-05-4) is a multifaceted compound with significant implications for pharmaceutical research and development. Its unique chemical properties, combined with its potential to address critical health challenges like antimicrobial resistance and sustainable synthesis, make it a focal point for ongoing investigations. As the scientific community continues to explore its applications, this compound is poised to remain a key player in the advancement of medicinal chemistry and drug discovery.

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