N-[4-(hydroxymethyl)-3-(trifluoromethyl)phenyl]-3-iodo-4-methylbenzamide
[CAS# 1488423-79-5]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: N-[4-(hydroxymethyl)-3-(trifluoromethyl)phenyl]-3-iodo-4-methylbenzamide
• Molecular Formula: C₁₆H₁₃F₃INO₂
• Molecular Weight: 435.18
• CAS Registry Number: 1488423-79-5
• SMILES: CC1=C(C=C(C=C1)C(=O)NC2=CC(=C(C=C2)CO)C(F)(F)F)I

Discovery and Applications

N-[4-(hydroxymethyl)-3-(trifluoromethyl)phenyl]-3-iodo-4-methylbenzamide is a substituted benzamide derivative containing multiple functional groups that contribute to its chemical reactivity and usefulness in synthetic and medicinal chemistry research. The molecule consists of two aromatic rings connected through an amide linkage. One ring bears a hydroxymethyl substituent and a trifluoromethyl group, while the other contains iodine and methyl substituents. Such structural features are commonly introduced in aromatic amides to influence electronic properties, steric effects, and interactions with biological targets. The study of benzamide derivatives has a long history in organic chemistry and pharmaceutical research. Benzamide itself was identified in the nineteenth century during investigations into aromatic amide compounds. Over time, systematic substitution on the benzamide framework became an important strategy for exploring chemical reactivity and biological activity. By the mid-twentieth century, benzamide derivatives had been extensively examined in medicinal chemistry, leading to the development of compounds with antipsychotic, antiemetic, and other pharmacological properties. These investigations demonstrated that substitution on the aromatic rings and modification of the amide nitrogen can significantly alter biological activity. The compound N-[4-(hydroxymethyl)-3-(trifluoromethyl)phenyl]-3-iodo-4-methylbenzamide reflects several design strategies used in modern synthetic chemistry. The presence of the trifluoromethyl group is particularly important because fluorinated substituents are known to influence lipophilicity, metabolic stability, and electronic distribution in aromatic molecules. Since the introduction of fluorine-containing groups into pharmaceuticals became widespread in the latter half of the twentieth century, many synthetic programs have incorporated trifluoromethyl substituents to modify chemical and biological properties. The iodine atom present on the benzamide ring also plays an important role in chemical synthesis. Aryl iodides are well known for their high reactivity in cross-coupling reactions, including palladium-catalyzed processes used to form carbon–carbon and carbon–heteroatom bonds. Because iodine is a good leaving group in such reactions, iodinated aromatic compounds are frequently used as intermediates in the preparation of more complex molecules. In this context, benzamide derivatives bearing iodine substituents can serve as valuable starting materials for the construction of diversified aromatic frameworks. The hydroxymethyl group attached to the phenyl ring provides an additional site for chemical transformation. Alcohol groups can undergo oxidation, esterification, or substitution reactions, allowing further modification of the molecule. Such functional groups are often introduced deliberately to provide synthetic flexibility in multistep organic synthesis. Compounds structurally related to this benzamide derivative have been described in chemical and pharmaceutical research as intermediates or candidates in drug discovery programs. Aromatic amides with halogen and fluorinated substituents have been synthesized and evaluated in studies investigating enzyme inhibition, receptor binding, and other biological activities. The combination of halogen substitution, fluorinated groups, and amide linkages is frequently encountered in medicinal chemistry because these features can influence molecular recognition and binding interactions. Analytical characterization of molecules such as N-[4-(hydroxymethyl)-3-(trifluoromethyl)phenyl]-3-iodo-4-methylbenzamide typically involves spectroscopic and analytical techniques including nuclear magnetic resonance spectroscopy, infrared spectroscopy, and mass spectrometry. These methods confirm the presence of the amide bond, aromatic substituents, and other functional groups. Structural analysis using crystallographic methods has also been applied to related benzamide derivatives to determine molecular geometry and intermolecular interactions in the solid state. The documented synthesis and investigation of substituted benzamides illustrate the continuing importance of aromatic amide chemistry in both synthetic methodology and pharmaceutical research. N-[4-(hydroxymethyl)-3-(trifluoromethyl)phenyl]-3-iodo-4-methylbenzamide represents a structurally defined example within this broad and well-established class of compounds.

References

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