Cas no 81265-32-9 (2,2,2-Trifluoroethyl 1H-imidazole-1-carboxylate)

2,2,2-Trifluoroethyl 1H-imidazole-1-carboxylate is a versatile trifluoroethyl ester derivative of imidazole-1-carboxylic acid, primarily employed as an intermediate in organic synthesis and pharmaceutical applications. Its key advantages include its reactivity as a carbonylating agent, enabling efficient introduction of the imidazole-1-carboxylate moiety into target molecules. The trifluoroethyl group enhances stability and influences electronic properties, making it valuable in the synthesis of heterocyclic compounds and active pharmaceutical ingredients (APIs). This compound is particularly useful in peptide coupling and protecting group strategies due to its selective reactivity. Its high purity and consistent performance under controlled conditions make it a reliable choice for research and industrial-scale processes.
2,2,2-Trifluoroethyl 1H-imidazole-1-carboxylate structure
81265-32-9 structure
Product Name:2,2,2-Trifluoroethyl 1H-imidazole-1-carboxylate
CAS No:81265-32-9
MF:C6H5F3N2O2
MW:194.111311674118
CID:725787
PubChem ID:133643
Update Time:2025-11-07

2,2,2-Trifluoroethyl 1H-imidazole-1-carboxylate Chemical and Physical Properties

Names and Identifiers

    • 1H-Imidazole-1-carboxylicacid, 2,2,2-trifluoroethyl ester
    • 2,2,2-trifluoroethyl imidazole-1-carboxylate
    • N-(2,2,2-trifluoroethoxycarbonyl)imidazole
    • VHSLGTPKFRBITL-UHFFFAOYSA-N
    • MFCD25967441
    • 1H-Imidazole-1-carboxylic acid, 2,2,2-trifluoroethyl ester
    • 81265-32-9
    • DTXSID00231014
    • 2,2,2-Tfi
    • 2,2,2-trifluoroethyl1H-imidazole-1-carboxylate
    • SCHEMBL12185258
    • 2,2,2-trifluoroethyl 1H-imidazole-1-carboxylate
    • 2,2,2-Trifluoroethyl 1H-imidazole-1-carboxylate
    • Inchi: 1S/C6H5F3N2O2/c7-6(8,9)3-13-5(12)11-2-1-10-4-11/h1-2,4H,3H2
    • InChI Key: VHSLGTPKFRBITL-UHFFFAOYSA-N
    • SMILES: FC(COC(N1C=NC=C1)=O)(F)F

Computed Properties

  • Exact Mass: 194.03
  • Monoisotopic Mass: 194.03
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 195
  • 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: 1.2
  • Topological Polar Surface Area: 44.1?2

Experimental Properties

  • Density: 1.44
  • Boiling Point: 211.3°C at 760 mmHg
  • Flash Point: 81.6°C
  • Refractive Index: 1.464

2,2,2-Trifluoroethyl 1H-imidazole-1-carboxylate Pricemore >>

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Additional information on 2,2,2-Trifluoroethyl 1H-imidazole-1-carboxylate

Comprehensive Overview of 2,2,2-Trifluoroethyl 1H-imidazole-1-carboxylate (CAS No. 81265-32-9)

2,2,2-Trifluoroethyl 1H-imidazole-1-carboxylate (CAS No. 81265-32-9) is a specialized organic compound that has garnered significant attention in pharmaceutical and agrochemical research due to its unique trifluoroethyl and imidazole functional groups. This compound is widely recognized for its role as an intermediate in the synthesis of bioactive molecules, particularly those targeting enzyme inhibition and receptor modulation. Its carboxylate moiety further enhances its reactivity, making it a versatile building block in modern synthetic chemistry.

In recent years, the demand for fluorinated compounds like 2,2,2-Trifluoroethyl 1H-imidazole-1-carboxylate has surged, driven by their applications in drug discovery and material science. Researchers are particularly interested in its potential to improve the metabolic stability and bioavailability of therapeutic agents. The trifluoroethyl group is known to impart electron-withdrawing properties, which can significantly alter the pharmacokinetic profiles of drug candidates. This aligns with current trends in precision medicine, where structure-activity relationships (SAR) are meticulously optimized for enhanced efficacy.

From an industrial perspective, CAS No. 81265-32-9 is often discussed in the context of green chemistry and sustainable synthesis. Manufacturers are increasingly adopting eco-friendly protocols to produce such intermediates, minimizing waste and energy consumption. This resonates with global initiatives like the UN Sustainable Development Goals (SDGs), particularly Goal 12 (Responsible Consumption and Production). Analytical techniques such as HPLC and NMR are routinely employed to ensure the purity and consistency of this compound, addressing quality concerns raised by regulatory bodies.

The compound’s imidazole ring also makes it a subject of interest in heterocyclic chemistry, a field that dominates contemporary organic synthesis. Imidazole derivatives are pivotal in designing antifungal and antiviral agents, reflecting the growing need for novel antimicrobials amid rising drug resistance. Additionally, its carbamate linkage offers stability under physiological conditions, a feature highly valued in prodrug development. These attributes have spurred discussions in academic forums and patent literature, highlighting its cross-disciplinary relevance.

For laboratory use, 2,2,2-Trifluoroethyl 1H-imidazole-1-carboxylate is typically handled under controlled conditions to preserve its integrity. Storage recommendations often include inert atmospheres and low temperatures, as the trifluoroethyl moiety may be sensitive to hydrolysis. Safety data sheets (SDS) provide detailed guidelines, emphasizing the importance of personal protective equipment (PPE) during handling. Such precautions align with broader workplace safety trends, especially in GMP-compliant facilities.

In summary, CAS No. 81265-32-9 represents a critical intersection of innovation and practicality in chemical research. Its applications span from medicinal chemistry to material science, driven by the evolving needs of industries and academia. As synthetic methodologies advance, this compound is poised to play an even greater role in addressing challenges like drug delivery and molecular design, cementing its status as a cornerstone of modern organic synthesis.

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