99137-12-9

Basic information

• Product Name: 4-Chloro-N-(4-nitro-phenyl)-benzimidoyl chloride
• Synonyms: 4-Chloro-N-(4-nitro-phenyl)-benzimidoyl chloride
• CAS NO: 99137-12-9
• Molecular Weight: 295.125
• Mol File: 99137-12-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 4-Chloro-N-(4-nitro-phenyl)-benzimidoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-N-(4-nitro-phenyl)-benzimidoyl chloride(99137-12-9)
• EPA Substance Registry System: 4-Chloro-N-(4-nitro-phenyl)-benzimidoyl chloride(99137-12-9)

Safety Data

• Hazardous Substances Data: 99137-12-9(Hazardous Substances Data)

Upstream product

• 39193-07-2 N-(4-nitrophenyl)-4-chlorophenyl carboxamide 

Downstream Products

• 13252-25-0 N-(4-chlorophenyl)-N'-(4-nitrophenyl)urea 
• 30152-32-0 3-(4?'-chlorophenyl)-5-phenyl-1H-pyrazole 

Relevant articles and documents

Light-Switchable Antagonists for the Histamine H1 Receptor at the Isolated Guinea Pig Ileum

The histamine H1 G protein-coupled receptor (GPCR) plays an important role in allergy and inflammation. Existing drugs that address the H1 receptor differ in their chemical structure, pharmacology, and side effects. Light-controllable spatial and temporal activity regulation of photochromic H1 ligands may contribute to a better mechanistic understanding and the development of improved correlations between ligand structure and pharmacologic effects. We report photochromic H1 receptor ligands, which were investigated in an organ-pharmacological assay. Initially, five photochromic azobenzene derivatives of reported dual H1–H4 receptor antagonists were designed, synthesized, photochemically characterized, and organ-pharmacologically tested on the isolated guinea pig ileum. Among them, one compound [trans-19: (Z)-1-(4-chlorophenyl)-1-(4-methylpiperazin-1-yl)-N-(4-((E)-phenyldiazenyl)phenyl)methanimine] retained the antagonistic activity of its non-photochromic lead, and trans–cis isomerization by irradiation induced a fourfold difference in the pharmacological response. Further structural optimization resulted in two bathochromically shifted derivatives of 19 [NO2-substituted 35 {(Z)-1-(4-chlorophenyl)-1-(4-methylpiperazin-1-yl)-N-(4-((E)-(4-nitrophenyl)diazenyl)phenyl)methanimine} and SO3?-substituted 41 {4-((E)-(4-(((Z)-(4-chlorophenyl)(4-methylpiperazin-1-yl)methylene)amino)phenyl)diazenyl)benzenesulfonate}], which do not require the use of UV light for photoisomerization and which also have improved solubility and show reduced tissue impairment. The trans isomers of both compounds showed a remarkable increase in antagonistic activity relative to their lead trans-19; furthermore, a 46-fold difference in activity on the isolated guinea pig ileum was observed between trans- and cis-35.