4-Hydroxy-2-methyl-1-(phenylmethyl)-1H-benzimidazole-6-carboxylic acid
[CAS# 1640981-19-6]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 4-Hydroxy-2-methyl-1-(phenylmethyl)-1H-benzimidazole-6-carboxylic acid
• Synonyms: 3-benzyl-7-hydroxy-2-methylbenzimidazole-5-carboxylic acid; 1-benzyl-4-hydroxy-2-methyl-1H-1,3-benzodiazole-6-carboxylic acid
• Molecular Formula: C₁₆H₁₄N₂O₃
• Molecular Weight: 282.29
• CAS Registry Number: 1640981-19-6
• SMILES: CC1=NC2=C(N1CC3=CC=CC=C3)C=C(C=C2O)C(=O)O

Properties

• Solubility: Practically insoluble (0.065 g/L) (25 ºC), Calc.^*
• Density: 1.33±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.661, Calc.^*
• Boiling Point: 601.5±50.0 ºC (760 mmHg), Calc.^*
• Flash Point: 317.6±30.1 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovory and Applicatios

4-Hydroxy-2-methyl-1-(phenylmethyl)-1H-benzimidazole-6-carboxylic acid is a complex organic compound that belongs to the class of substituted benzimidazoles. The benzimidazole core structure consists of a fused ring system containing nitrogen atoms, which is known for its diverse biological and chemical properties. This particular compound features a hydroxyl group at the 4-position, a methyl group at the 2-position, and a phenylmethyl group at the 1-position, with a carboxylic acid group at the 6-position. The presence of these functional groups makes it a versatile molecule with a range of potential applications in medicinal chemistry, material science, and organic synthesis.

The discovery of 4-hydroxy-2-methyl-1-(phenylmethyl)-1H-benzimidazole-6-carboxylic acid is rooted in the broader exploration of benzimidazole derivatives, which have been studied extensively due to their structural resemblance to purine and other biologically significant molecules. The benzimidazole ring system is known to exhibit a range of biological activities, including antimicrobial, anti-inflammatory, and anticancer properties. Researchers have been interested in modifying the benzimidazole structure by adding various substituents to enhance or tailor its pharmacological activity. In particular, the introduction of a hydroxyl group, methyl group, and phenylmethyl group to the benzimidazole core has been studied to optimize its interaction with biological targets.

Synthetically, 4-hydroxy-2-methyl-1-(phenylmethyl)-1H-benzimidazole-6-carboxylic acid can be prepared through several routes. One common method involves the condensation of an appropriate substituted aniline with an aldehyde or ketone, followed by a cyclization reaction to form the benzimidazole ring system. The functional groups on the benzimidazole ring, such as the hydroxyl and carboxylic acid groups, can be introduced through specific reactions involving reagents that allow for selective functionalization of the aromatic ring. Purification techniques such as chromatography are used to isolate the desired product from the reaction mixture.

The applications of 4-hydroxy-2-methyl-1-(phenylmethyl)-1H-benzimidazole-6-carboxylic acid are primarily found in the fields of medicinal chemistry and drug development. The presence of the hydroxyl and carboxylic acid functional groups makes it a promising candidate for the design of drugs that can interact with specific biological targets, such as enzymes or receptors. Benzimidazole derivatives have been investigated for their potential as antimicrobial agents, and compounds similar to 4-hydroxy-2-methyl-1-(phenylmethyl)-1H-benzimidazole-6-carboxylic acid could exhibit activity against bacterial or fungal infections. Additionally, the anticancer potential of benzimidazole derivatives has been widely studied, and this compound may have similar applications due to its ability to interfere with cell division processes.

In addition to its potential as a drug candidate, 4-hydroxy-2-methyl-1-(phenylmethyl)-1H-benzimidazole-6-carboxylic acid may have applications in materials science. The stability and chemical reactivity of benzimidazole derivatives make them useful in the development of organic semiconductors and other advanced materials. Research into their properties in electronic devices, such as light-emitting diodes (LEDs) or solar cells, continues to expand as scientists explore the utility of these compounds in emerging technologies.

In conclusion, 4-hydroxy-2-methyl-1-(phenylmethyl)-1H-benzimidazole-6-carboxylic acid is a promising compound with potential applications in medicinal chemistry, drug development, and materials science. Its unique structure and biological activity make it a valuable subject for further research, with the possibility of contributing to the development of new therapeutic agents and advanced materials.