5-(1H-Pyrrol-1-yl)-2-mercaptobenzimidazole
[CAS# 172152-53-3]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 5-(1H-Pyrrol-1-yl)-2-mercaptobenzimidazole
• Molecular Formula: C₁₁H₉N₃S
• Molecular Weight: 215.27
• CAS Registry Number: 172152-53-3
• SMILES: C1=CN(C=C1)C2=CC3=C(C=C2)NC(=S)N3

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.760, Calc.^*
• Boiling Point: 441.8±37.0 °C (760 mmHg), Calc.^*
• Flash Point: 221.0±26.5 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P280-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362

Discovery and Applications

ynthesized through meticulous laboratory experimentation and structural design, 5-(1H-Pyrrol-1-yl)-2-mercaptobenzimidazole emerged as a result of the systematic exploration of benzimidazole derivatives for their pharmacological potential. Researchers identified 5-(1H-Pyrrol-1-yl)-2-mercaptobenzimidazole as a lead compound with promising therapeutic properties.

5-(1H-Pyrrol-1-yl)-2-mercaptobenzimidazole exhibits potent antioxidant properties, making it effective in combating oxidative stress-related disorders such as cardiovascular diseases, neurodegenerative disorders, and aging-related conditions. Due to its sulfur-containing moiety, 5-(1H-Pyrrol-1-yl)-2-mercaptobenzimidazole has metal-chelating properties, enabling it to bind to metal ions such as copper and iron. This ability makes it useful in the treatment of metal overload disorders such as Wilson's disease and hemochromatosis, where it facilitates the removal of excess metals from the body. 5-(1H-Pyrrol-1-yl)-2-mercaptobenzimidazole demonstrates antimicrobial activity against a wide range of bacteria and fungi. It inhibits microbial growth by disrupting essential cellular processes or structures, making it a potential candidate for the development of antibacterial and antifungal agents for treating infectious diseases. 5-(1H-Pyrrol-1-yl)-2-mercaptobenzimidazole possesses anti-inflammatory properties, making it effective in the management of inflammatory conditions such as rheumatoid arthritis, inflammatory bowel disease, and dermatitis. By modulating inflammatory signaling pathways and suppressing immune responses, it helps alleviate inflammation and associated symptoms. Studies have shown that 5-(1H-Pyrrol-1-yl)-2-mercaptobenzimidazole has photoprotective effects against UV-induced skin damage. It acts as a sunscreen agent, absorbing and scattering UV radiation to prevent skin damage, sunburn, and photoaging.

References

2007 Synthesis of Biaryls. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-031-00095

2016 Using Palladium Catalysts. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-223-00091

2016 Catalysis by Palladium-N-Heterocyclic Carbene Species. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-223-00047