4-(5-Amino-1-methyl-1H-benzoimidazol-2-yl)-butyric acid isopropyl ester
[CAS# 1313020-26-6]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 4-(5-Amino-1-methyl-1H-benzoimidazol-2-yl)-butyric acid isopropyl ester
• Synonyms: propan-2-yl 4-(5-amino-1-methylbenzimidazol-2-yl)butanoate
• Molecular Formula: C₁₅H₂₁N₃O₂
• Molecular Weight: 275.35
• CAS Registry Number: 1313020-26-6
• SMILES: CC(C)OC(=O)CCCC1=NC2=C(N1C)C=CC(=C2)N

Properties

• Density: 1.2$+/-$0.1 g/cm³ Calc.^*
• Boiling point: 473.9$+/-$25.0 $degree$C 760 mmHg (Calc.)^*
• Flash point: 240.4$+/-$23.2 $degree$C (Calc.)^*
• Index of refraction: 1.584 (Calc.)^*

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

Discovery and Applications

4-(5-Amino-1-methyl-1H-benzoimidazol-2-yl)-butyric acid isopropyl ester is an organic compound belonging to the class of benzimidazole derivatives. Benzimidazole is a fused heterocyclic system consisting of a benzene ring joined to an imidazole ring, and it has been widely studied in organic and medicinal chemistry. The investigation of benzimidazole compounds dates back to the late nineteenth century, when chemists first synthesized and characterized the heterocyclic framework. Subsequent research in the twentieth century revealed that benzimidazole derivatives display a wide range of chemical and biological properties, which led to the preparation of numerous substituted analogs for pharmaceutical and biochemical studies. The compound 4-(5-amino-1-methyl-1H-benzimidazol-2-yl)-butyric acid isopropyl ester contains a benzimidazole nucleus substituted with an amino group and a methyl group on the heterocyclic ring system. In addition, the benzimidazole ring is connected through the 2-position to a butyric acid side chain that is present in the form of an isopropyl ester. Structural modification of the benzimidazole core through substitution at the 2-position has been a common strategy in heterocyclic chemistry, as this position allows the attachment of aliphatic or aromatic groups that can influence chemical reactivity and biological activity. Research on substituted benzimidazoles expanded significantly during the mid-twentieth century as chemists explored their potential as biologically active molecules. The benzimidazole ring resembles structural features found in naturally occurring purine bases and other biologically important heterocycles. Because of this structural similarity, benzimidazole derivatives have been investigated as potential pharmacologically active agents. Numerous compounds containing the benzimidazole scaffold have been synthesized and examined for antimicrobial, antiparasitic, antiviral, and anticancer properties. These investigations led to the discovery and development of several clinically useful drugs belonging to the benzimidazole class. Derivatives bearing amino substituents on the aromatic ring have attracted particular attention because such functional groups can participate in hydrogen bonding and other interactions with biological macromolecules. The presence of a butyric acid side chain attached to the benzimidazole nucleus provides additional chemical versatility. Esterification of the carboxylic acid to form the isopropyl ester can influence the compound’s solubility and stability, and ester groups are frequently used in synthetic chemistry as intermediates that can later be hydrolyzed to regenerate the corresponding acid. Compounds related to 4-(5-amino-1-methyl-1H-benzimidazol-2-yl)-butyric acid derivatives have been described in chemical and pharmaceutical research as intermediates in the synthesis of more complex heterocyclic molecules. The benzimidazole ring system serves as a versatile building block in the preparation of compounds designed for biological testing. Synthetic routes typically involve formation of the benzimidazole nucleus through condensation reactions of o-phenylenediamine derivatives with suitable carbonyl compounds, followed by further functionalization at specific positions on the ring. Beyond pharmaceutical research, benzimidazole derivatives have also been investigated for applications in coordination chemistry and materials science. The nitrogen atoms within the heterocyclic ring can act as coordination sites for metal ions, allowing such molecules to participate in the formation of metal complexes. These complexes have been examined for their structural properties and potential catalytic or electronic behavior. The study and synthesis of substituted benzimidazole compounds therefore form an established area of heterocyclic chemistry. 4-(5-Amino-1-methyl-1H-benzoimidazol-2-yl)-butyric acid isopropyl ester represents a structurally defined member of this broader class, reflecting the continuing interest in modifying the benzimidazole framework to explore its chemical reactivity and potential applications in scientific research.

References

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URL: https://patents.google.com/patent/US9376394B2/en

2011. Preparation of bendamustine and its salts. WO-2011079193-A2.
URL: https://patents.google.com/patent/WO2011079193A2/en