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
• Article Data: 2

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

General Description

6-Chlorobenzimidazole-4-carboxylic acid is a chemical compound with the molecular formula C8H5ClN2O2. It is a derivative of benzimidazole and has a chlorine atom attached to the benzene ring. 6-CHLOROBENZIMIDAZOLE-4-CARBOXYLIC ACID is used in organic synthesis and medicinal chemistry as a building block for the synthesis of pharmaceuticals and bioactive compounds. It has shown potential antibacterial and antifungal properties, making it a valuable compound in the development of new drugs. Its carboxylic acid functional group also makes it useful in the synthesis of various derivatives with different biological activities.

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.