News

Uses of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline (CAS No. 641571-11-1) is a versatile compound with significant applications in pharmaceuticals, chemical synthesis, and materials science.

1. Pharmaceutical Intermediate

• Key Role in Anticancer Drug Synthesis: This compound serves as a crucial intermediate in the production of nilotinib, a second-generation tyrosine kinase inhibitor (TKI) used to treat chronic myeloid leukemia (CML) and Philadelphia chromosome-positive acute lymphoblastic leukemia (Ph+ ALL). Nilotinib works by inhibiting the BCR-ABL protein, a driver mutation in these cancers.
• Synthetic Pathway: It is integrated into nilotinib’s synthesis via coupling reactions, contributing to the drug’s core structure. Its trifluoromethyl and imidazole groups enhance binding affinity to the target enzyme, improving therapeutic efficacy.

2. Chemical Synthesis

• Building Block for Heterocyclic Compounds: The molecule’s imidazole and trifluoromethyl moieties make it a valuable precursor for synthesizing other bioactive heterocycles, such as:
  • Antimicrobial Agents: Modified derivatives exhibit activity against bacteria and fungi.
  • Antiviral Compounds: Potential in developing inhibitors for viral enzymes.
• Cross-Coupling Reactions: Its aromatic amine group enables Pd-catalyzed couplings (e.g., Suzuki-Miyaura, Buchwald-Hartwig), facilitating the attachment of diverse functional groups.

3. Material Science

• Functional Materials: Incorporated into polymers or coatings to impart specific properties, such as:
  • Antimicrobial Surfaces: When embedded in medical devices or textiles, it helps prevent microbial colonization.
  • Electronic Materials: Potential use in organic electronics due to its conjugated system and tunable electronic properties.

4. Research and Development

• Drug Discovery: Screened in high-throughput assays to identify leads for treating cancers, inflammatory diseases, or neurological disorders.
• Mechanistic Studies: Used as a probe to investigate enzyme-ligand interactions, particularly in kinase inhibition.

5. Advantages in Synthesis

• Stability: The trifluoromethyl group enhances metabolic stability, reducing degradation in biological systems.
• Reactivity: The imidazole ring and amine functionality allow for diverse chemical transformations, enabling the synthesis of complex molecules.

6. Challenges and Considerations

• Toxicity: While essential in pharmaceuticals, its use requires careful handling due to potential hazards. Safety protocols must be followed in laboratory and industrial settings.
• Regulatory Compliance: Synthesis and application must adhere to strict guidelines, especially in pharmaceuticals, to ensure product quality and patient safety.

7. Emerging Applications

• Agrochemicals: Explored as a precursor for herbicides or insecticides, leveraging its bioactive potential.
• Bioconjugation: Facilitates site-specific labeling of biomolecules for imaging or therapeutic delivery.