4-Amino-3-nitropyridine Chemical Properties

Melting point:

203-207 °C (lit.)

Boiling point:

255.04°C (rough estimate)

Density 

1.4551 (rough estimate)

refractive index 

1.5900 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

Crystalline Powder

pka

5.02±0.12(Predicted)

color 

Yellow

Water Solubility 

Insoluble in water.

BRN 

383710

InChI

InChI=1S/C5H5N3O2/c6-4-1-2-7-3-5(4)8(9)10/h1-3H,(H2,6,7)

InChIKey

IUPPEELMBOPLDJ-UHFFFAOYSA-N

SMILES

C1=NC=CC(N)=C1[N+]([O-])=O

CAS DataBase Reference

1681-37-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38-20/21/22

Safety Statements 

26-36-36/37/39

RIDADR 

UN2811

WGK Germany 

3

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Amino-3-nitropyridine Usage And Synthesis

Chemical Properties

yellow crystalline powder

Uses

4-Amino-3-nitropyridine is used as a pharmaceutical intermediate.

Synthesis

The general procedure for the synthesis of 4-amino-3-nitropyridine from 4-aminopyridine was as follows: pyridin-4-amine (5.0 g, 50.0 mmol) was dissolved in concentrated sulfuric acid (20 mL) under ice-bath conditions. Keeping the reaction temperature in the range of 0-10 °C, fuming nitric acid (2.5 mL) was added slowly and dropwise. After the dropwise addition, the reaction was continued to be stirred at 0-10 °C for 5 hours. Subsequently, the reaction mixture was warmed to room temperature and heated at 90°C for 3 hours. After the reaction was completed, the mixture was continued to be stirred at room temperature overnight. The reaction mixture was slowly poured into ice water and the pH was adjusted with ammonia to 7. The resulting precipitate was collected by filtration and dried under reduced pressure to afford 4-amino-3-nitropyridine as a yellow solid (5.1 g, 70% yield). Mass spectrometry analysis showed [M + H]+ m/z: 140.04.

References

[1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 9, p. 2621 - 2631
[2] Synthesis, 2011, # 5, p. 794 - 806
[3] Chemistry of Heterocyclic Compounds, 2015, vol. 51, # 2, p. 203 - 204
[4] Khim. Geterotsikl. Soedin., 2015, vol. 51, # 2, p. 203 - 204,2
[5] Patent: WO2017/168333, 2017, A1. Location in patent: Page/Page column 16

4-Amino-3-nitropyridine(1681-37-4)Related Product Information

• 3-Aminopyridine
• 4-Methyl-3-nitropyridine
• 6-Aminocaproic acid
• 4-Amino-3-nitrophenol
• ALTRENOGEST
• 3-Nitropyridine
• 3-Aminophenol
• 4-Dimethylaminopyridine
• 4-Aminopyridine
• 4-Amino-3-nitrobenzonitrile
• Glycine
• 5-Amino-2-methylpyridine
• Tris(hydroxymethyl)aminomethane
• 2-Amino-3-nitropyridine ,99%,2-AMINO-3-NITROPYRIDINE
• Elbanizine
• 4-AMINO-3-NITROQUINOLINE
• 4-HYDRAZINO-3-NITROPYRIDINE
• 4-(DIMETHYLAMINO)-3-NITROPYRIDINE