203794-33-6

Basic information

• Product Name: 5,6-dichloro-3-nitropyridin-2-aMine
• Synonyms: 5,6-dichloro-3-nitropyridin-2-aMine;5,6-dichloro-2-amino-3-nitropyridine;5,6-Dichloro-3-nitro-2-pyridinamine
• CAS NO: 203794-33-6
• Molecular Formula: C₅H₃Cl₂N₃O₂
• Molecular Weight: 208.00222
• Mol File: 203794-33-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 347.1±37.0 °C(Predicted)
• Appearance: /
• Density: 1.723±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: -3.87±0.50(Predicted)
• CAS DataBase Reference: 5,6-dichloro-3-nitropyridin-2-aMine(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-dichloro-3-nitropyridin-2-aMine(203794-33-6)
• EPA Substance Registry System: 5,6-dichloro-3-nitropyridin-2-aMine(203794-33-6)

Safety Data

• Hazardous Substances Data: 203794-33-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
5,6-dichloro-3-nitropyridin-2-amine is utilized as a key intermediate in the synthesis of pharmaceuticals. Its unique structure allows for the development of new drugs with specific therapeutic properties, making it a valuable component in medicinal chemistry.
Used in Agrochemical Synthesis:
In the agrochemical industry, 5,6-dichloro-3-nitropyridin-2-amine serves as a crucial building block for the creation of new pesticides and other agrochemicals. Its incorporation into these products can enhance their effectiveness in controlling pests and diseases in agriculture.
Used in Organic Chemistry Research:
5,6-dichloro-3-nitropyridin-2-amine also has potential applications as a building block in organic chemistry research. Its versatile structure allows for further functionalization and modification, enabling the exploration of new chemical reactions and the synthesis of novel organic compounds.
Safety Considerations:
Due to its toxic and potentially harmful properties, 5,6-dichloro-3-nitropyridin-2-amine is classified as a hazardous substance. It should be handled with care, following proper safety protocols to minimize risks to human health and the environment.

Upstream product

• 45644-21-1 6-chloropyridin-2-amine 

Downstream Products

• 1394374-31-2 tert-butyl 4-((4-(2-(((3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)oxy)-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-5-yl)phenyl)ethynyl)piperidine-1-carboxylate 
• 1394374-18-5 2-(((3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)oxy)-6-chloro-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridine 
• 1394374-15-2 5-(4-bromophenyl)-2-(((3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)oxy)-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridine 
• 1394374-10-7 2-[[2-[[(3R,3aR,6S,6aS)-6-fluoro-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]oxy]-6-chloro-5-(4-phenylphenyl)imidazo[4,5-b]pyridin-1-yl]methoxy]ethyl-trimethyl-silane 
• 1394374-06-1 2-[1-[5-[4-[2-[[(3R,3aR,6R,6aR)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]oxy]-6-chloro-1H-imidazo[4,5-b]pyridin-5-yl]phenyl]-2-pyridyl]pyrazol-4-yl]acetic acid 
• 1394374-04-9 methyl 2-[1-[5-[4-[2-[[(3R,3aR,6R,6aR)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]oxy]-6-chloro-1-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-5-yl]phenyl]-2-pyridyl]pyrazol-4-yl]acetate 
• 1394374-02-7 2-[1-[5-[4-[2-[[(3R,3aR,6R,6aR)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]oxy]-6-chloro-1-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-5-yl]phenyl]-2-pyridyl]pyrazol-4-yl]acetic acid 
• 1394374-00-5 (3R,3aR,6R,6aR)-6-[6-chloro-5-[4-[6-(1,2,4-triazol-1-yl)-3-pyridyl]phenyl]-1-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol 
• 1394373-98-8 (3R,3aR,6R,6aR)-6-[6-chloro-5-[4-[5-[4-(2-hydroxy-2-methyl-propyl)pyrazol-1-yl]-2-pyridyl]phenyl]-1-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol 
• 1394373-96-6 methyl 2-[1-[6-[4-[2-[[(3R,3aR,6R,6aR)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]oxy]-6-chloro-1-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-5-yl]phenyl]-3-pyridyl]pyrazol-4-yl]acetate 
• 1394373-94-4 2-[1-[6-[4-[2-[[(3R,3aR,6R,6aR)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]oxy]-6-chloro-1-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-5-yl]phenyl]-3-pyridyl]pyrazol-4-yl]acetic acid 
• 1394373-92-2 (3R,3aR,6R,6aR)-6-[6-chloro-5-[4-(5-pyrazol-1-yl-2-pyridyl)phenyl]-1-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol 

Relevant articles and documents

Design, synthesis and anti-HBV activity evaluation of new substituted imidazo[4,5-b]pyridines

The design and synthesis of a number of new imidazo[4,5-b]pyridines is described. The heterocyclic scaffold possesses 6-chloro- or 5,6-dichloro-substitution and bears various 2-alkylamino-methyl or ethyl groups. The corresponding N1 and N3-tosylates are also presented. The anti-HBV activity of the compounds was evaluated in HBV infectious system at the level of HBV rcDNA secretion and CC50, EC50 and selectivity index values were determined. The tosylates showed low antiviral potency and relatively high cytotoxicity, on the contrary, a number of 2,5 and/or-6-substituted imidazopyridines, mainly those belonging to the 6-chloroimidazo[4,5-b]pyridine series, were endowed with a very interesting profile and were further investigated. The most promising among them, along with the reduction of the secreted HBV rcDNA, also caused a reduction in HBV cccDNA and pgRNA levels, with a concomitant accumulation of the intracellular encapsidated rcDNA. Surprisingly, the most active 2-diethylaminoethyl-substituted derivative (21d), was highly competitive to interferon.

Synthesis of new imidazopyridine nucleoside derivatives designed as maribavir analogues

The strong inhibition of Human Cytomegalovirus (HCMV) replication by benzimidazole nucleosides, like Triciribine and Maribavir, has prompted us to expand the structure-activity relationships of the benzimidazole series, using as a central core the imidazo[4,5-b]pyridine scafflold. We have thus synthesized a number of novel amino substituted imidazopyridine nucleoside derivatives, which can be considered as 4-(or 7)-aza-d-isosters of Maribavir and have evaluated their potential antiviral activity. The target compounds were synthesized upon glycosylation of suitably substituted 2-aminoimidazopyridines, which were prepared in six steps starting from 2-amino-6-chloropyridine. Even if the new compounds possessed only a slight structural modification when compared to the original drug, they were not endowed with interesting antiviral activity. Even so, three derivatives showed promising cytotoxic potential.