86309-90-2

Basic information

• Product Name: N-(4-Chloro-2-nitrophenyl)diethylamine
• Synonyms: N-(4-Chloro-2-nitrophenyl)diethylamine
• CAS NO: 86309-90-2
• Molecular Weight: 228.678
• Mol File: 86309-90-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(4-Chloro-2-nitrophenyl)diethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-Chloro-2-nitrophenyl)diethylamine(86309-90-2)
• EPA Substance Registry System: N-(4-Chloro-2-nitrophenyl)diethylamine(86309-90-2)

Safety Data

• Hazardous Substances Data: 86309-90-2(Hazardous Substances Data)

Upstream product

• 2873-89-4 4-chloro-N,N-diethylaniline 
• 345-18-6 2-fluoro-5-chloronitrobenzene 
• 109-89-7 diethylamine 
• 106-47-8 4-chloro-aniline 
• 89-61-2 2,5-dichloronitrobenzene 
• 67-56-1 methanol 

Downstream Products

• 901273-35-6 4-chloro-N₁,N₁-diethylbenzene-1,2-diamine 
• 28491-95-4 N-ethyl-4-chloro-2-nitro-aniline 
• 86309-91-3 (4-Chloro-2-nitrophenyl)ethylnitrosamine 

Relevant articles and documents

Optimisation of 2-(N-phenyl carboxamide) triazolopyrimidine antimalarials with moderate to slow acting erythrocytic stage activity

Malaria is a devastating parasitic disease caused by parasites from the genus Plasmodium. Therapeutic resistance has been reported against all clinically available antimalarials, threatening our ability to control the disease and therefore there is an ongoing need for the development of novel antimalarials. Towards this goal, we identified the 2-(N-phenyl carboxamide) triazolopyrimidine class from a high throughput screen of the Janssen Jumpstarter library against the asexual stages of the P. falciparum parasite. Here we describe the structure activity relationship of the identified class and the optimisation of asexual stage activity while maintaining selectivity against the human HepG2 cell line. The most potent analogues from this study were shown to exhibit equipotent activity against P. falciparum multidrug resistant strains and P. knowlesi asexual parasites. Asexual stage phenotyping studies determined the triazolopyrimidine class arrests parasites at the trophozoite stage, but it is likely these parasites are still metabolically active until the second asexual cycle, and thus have a moderate to slow onset of action. Non-NADPH dependent degradation of the central carboxamide and low aqueous solubility was observed in in vitro ADME profiling. A significant challenge remains to correct these liabilities for further advancement of the 2-(N-phenyl carboxamide) triazolopyrimidine scaffold as a potential moderate to slow acting partner in a curative or prophylactic antimalarial treatment.

Stereoelectronic Effects in Tertiary Amine Nitrosation: Nitrosative Cleavage vs. Aryl Ring Nitration

The nitrosation (acetic acid) of N-(4-chlorophenyl)pyrrolidine gives at least 30percent N-(4-chloro-2-nitrophenyl)pyrrolidine while the corresponding aryldibenzylamine gives no nitration and only nitrosative dealkylation at nitrogen.This difference in reaction site has been probed with N-(4-chlorophenyl)diethylamine.This substance undergoes competitive ring nitration to N-(4-chloro-2-nitrophenyl)diethylamine (50percent) and nitrosative dealkylation to (4-chlorophenyl)ethylnitrosamine (50percent).The former compound nitrosates further to give (4-chloro-2-nitrophenyl)ethylnitrosamine.This substance denitrosates to give the corresponding secondary amine.The reactivity differences result from stereoelectronic factors controlling the amine nitrogen unshared pair delocalization into the aryl ring.This interpretation is supported by 13C NMR data and mechanistic arguments.