4-Amino-2-chloro-3-nitropyridine Chemical Properties

Melting point:

205-207 °C (decomp)

Boiling point:

392.8±37.0 °C(Predicted)

Density 

1.596±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

powder to crystal

pka

0.63±0.42(Predicted)

color 

White to Yellow

λmax

238nm(H2O)(lit.)

CAS DataBase Reference

2789-25-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-43-36/37/38

Safety Statements 

36/37-37/39-26

HS Code 

29333990

4-Amino-2-chloro-3-nitropyridine Usage And Synthesis

Chemical Properties

Yellow solid

Uses

4-Amino-2-chloro-3-nitropyridine is used as a reagent in the synthesis of imidazopyridine-based fatty acid synthase inhibitors which show anti-HCV activity. Also used as a reagent in the synthesis of acyclic nucleotides that are related to clitocine, which exhibit antiviral activity.

Synthesis

2-Chloro-4-nitroaminopyridine (CAS: 14432-13-4, 10.0 g) was used as a raw material, which was slowly dissolved in 100 mL of concentrated sulfuric acid at room temperature, followed by heating the reaction mixture to 100 °C and maintaining it for 1 hour. Upon completion of the reaction, the solution was cooled to room temperature and slowly poured into 250 g of crushed ice. The pH of the mixture was adjusted to 3 with concentrated ammonium hydroxide under cooling in an ice bath while ensuring that the temperature did not exceed 20°C. The precipitated yellow solid was separated by filtration and the aqueous phase was extracted with ethyl acetate (200 mL × 3). The organic layers were combined and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography with an eluent ratio of hexane:ethyl acetate (4:1 to pure ethyl acetate, v/v) to give 4-amino-2-chloro-3-nitropyridine (6.0 g, 70% yield) and 4-amino-2-chloro-5-nitropyridine (2.0 g, 25% yield). 4-amino-2-chloro-3-nitropyridine The physical properties were as follows: melting point 179-181 °C; UV (H2O) λmax 238.0 nm (ε 13586, pH 11); 1H-NMR (DMSO-d6, 500 MHz) δ 7.91 (d, J = 6.0 Hz, 1H), 7.37 (s, 2H), 6.83 (d, J = 6.0 Hz, 1H); 13C-NMR (DMSO-d6, 125 MHz) δ 149.54, 149.24, 142.69, 142.33, 122.45. 1H-NMR (DMSO-d6, 500 MHz) δ 8.85 (s, 1H), 7.37 (s, 2H), 6.96 (s, 1H) for 4-amino-2-chloro-5-nitropyridine.

References

[1] Patent: WO2007/47793, 2007, A2. Location in patent: Page/Page column 87
[2] Roczniki Chemii, 1956, vol. 30, p. 1139,1144
[3] Chem.Abstr., 1957, p. 12089
[4] Nucleosides, nucleotides and nucleic acids, 2004, vol. 23, # 1-2, p. 67 - 76
[5] Organic and Biomolecular Chemistry, 2013, vol. 11, # 38, p. 6526 - 6545

4-Amino-2-chloro-3-nitropyridine(2789-25-5)Related Product Information

• 3-Nitropyridine
• 5-Bromo-2-chloro-3-nitropyridine
• 1-Chloro-3-nitrobenzene
• 4-Dimethylaminopyridine
• 2-Chloro-3-cyanopyridine
• 2-Aminopyridine
• Epichlorohydrin
• Pentachloropyridine
• 3-Aminopyridine
• Clopidol
• Betaine
• 2-Chloro-3-pyridinamine
• 2-Chloro-5-chloromethylpyridine
• 4-Chloro-3-nitropyridine
• ALTRENOGEST
• Aniline
• Bis(2-ethylhexyl)amine
• Glycine