180569-27-1

Basic information

• Product Name: 6-CHLOROBENZIMIDAZOLE-4-CARBOXYLIC ACID
• Synonyms: 6-CHLOROBENZIMIDAZOLE-4-CARBOXYLIC ACID;1H-Benzimidazole-4-carboxylicacid,6-chloro-(9CI);5-chloro-1H-Benzimidazole-7-carboxylic acid;6-chloro-1H-benzimidazole-4-carboxylic acid;6-Chloro-1H-benzo[d]imidazole-4-carboxylic acid;6-chlorobenzo[d]imidazole-4-carboxylic acid
• CAS NO: 180569-27-1
• Molecular Formula: C8H5ClN2O2
• Molecular Weight: 196.59
• Product Categories: BENZIMIDAZOLE;pharmacetical
• Mol File: 180569-27-1.mol

Chemical Properties

• Boiling Point: 552.2 °C at 760 mmHg
• Flash Point: 287.8 °C
• Appearance: /
• Density: 1.644 g/cm³
• Vapor Pressure: 4.97E-13mmHg at 25°C
• Refractive Index: 1.744
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -0.23±0.10(Predicted)
• CAS DataBase Reference: 6-CHLOROBENZIMIDAZOLE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLOROBENZIMIDAZOLE-4-CARBOXYLIC ACID(180569-27-1)
• EPA Substance Registry System: 6-CHLOROBENZIMIDAZOLE-4-CARBOXYLIC ACID(180569-27-1)

Safety Data

• Hazardous Substances Data: 180569-27-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
6-Chlorobenzimidazole-4-carboxylic acid is utilized as a building block in organic synthesis for the creation of various pharmaceuticals and bioactive compounds. Its unique structure and functional group facilitate the development of new chemical entities with potential therapeutic applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 6-chlorobenzimidazole-4-carboxylic acid is employed as a key intermediate for the synthesis of drugs. Its presence in the molecular structure can influence the pharmacokinetics and pharmacodynamics of the resulting compounds, contributing to their efficacy and safety profiles.
Used in Antibacterial Applications:
6-Chlorobenzimidazole-4-carboxylic acid has demonstrated potential antibacterial properties, making it a valuable compound in the development of new antimicrobial agents. Its ability to inhibit bacterial growth can be harnessed to combat resistant strains and contribute to the treatment of various infections.
Used in Antifungal Applications:
Similarly, this compound has shown antifungal activity, positioning it as a candidate for the development of new antifungal drugs. Its potential to treat fungal infections can be particularly beneficial in addressing the growing issue of antifungal resistance.
Used in the Synthesis of Derivatives with Different Biological Activities:
The carboxylic acid functional group of 6-chlorobenzimidazole-4-carboxylic acid allows for the synthesis of various derivatives with a range of biological activities. This versatility can lead to the discovery of compounds with novel therapeutic effects and applications in different areas of medicine.

InChI:InChI=1/C8H5ClN2O2/c9-4-1-5(8(12)13)7-6(2-4)10-3-11-7/h1-3H,(H,10,11)(H,12,13)

Upstream product

• 180508-09-2 6-chloro-4-methylbenzimidazole 
• 109671-52-5 2-amino-5-chloro-3-methylaniline 

Relevant articles and documents

Benzimidazole derivatives. Part 1: Synthesis and structure-activity relationships of new benzimidazole-4-carboxamides and carboxylates as potent and selective 5-HT4 receptor antagonists

New benzimidazole-4-carboxamides 1-16 and -carboxylates 17-26 were synthesized and evaluated for binding affinity at serotonergic 5-HT4 and 5- HT3 receptors in the CNS. Most of the synthesized compounds exhibited moderate-to-very high affinity (in many cases subnanomolar) for the 5-HT4 binding site and no significant affinity for the 5-HT3 receptor. SAR observations and structural analyses (molecular modeling, INSIGHT II) indicated that the presence of a voluminous substituent in the basic nitrogen atom of the amino moiety and a distance of ca. 8.0 A from this nitrogen to the aromatic ring are of great importance for high affinity and selectivity for 5-HT4 receptors. These results confirm our recently proposed model for recognition by the 5-HT4 binding site. Amides 12-15 and esters 24 and 25 bound at central 5-HT4 sites with very high affinity (K(i) = 0.11-2.9 nM) and excellent selectivity over serotonin 5-HT3, 5-HT(2A), and 5-HT(1A) receptors (K(i) > 1000-10,000 nM). Analogues 12 (K(i)(5-HT4) = 0.32 nM), 13 (K(i)(5-HT4) = 0.11 nM), 14 (K(i)(5-HT4) = 0.29 nM) and 15 (K(i)(5-HT4) = 0.54 nM) were pharmacologically characterized as selective 5-HT4 antagonists in the isolated guinea pig ileum (pA2 = 7.6, 7.9, 8.2 and 7.9, respectively), with a potency comparable to the 5-HT4 receptor antagonist RS 39604 (pA2 = 8.2). The benzimidazole-4-carboxylic acid derivatives described in this paper represent a novel class of potent and selective 5-HT4 receptor antagonists. In particular, compounds 12-15 could be interesting pharmacological tools for the understanding of the role of 5-HT4 receptors. (C) 1999 Elsevier Science Ltd.

Novel benzimidazole-4-carboxylic acid derivatives as potent and selective 5-HT3 receptor ligands

A series of benzimidazole-4-carboxylic acid derivatives was synthesized and evaluated for affinity at 5-HT3 and 5-HT4 serotoninergic receptors. Compounds 1b, c and j exhibited high affinity for the 5-HT3 receptors (K(i)=6.1, 3.7 and 4.9 nM, respectively) and no significant affinity for 5- HT4 (K(i)>1000 nM) and 5-HT(1A) (K(i)>10 000 nM) sites. Preliminary studies showed that 1c displayed activity in the two-compartment behavioural model.