2-Amino-3-methyl-5-nitropyridine Chemical Properties

Melting point:

256-260 °C

Boiling point:

276.04°C (rough estimate)

Density 

1.3682 (rough estimate)

refractive index 

1.6500 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

3.13±0.49(Predicted)

form 

powder to crystal

color 

Light yellow to Yellow to Orange

BRN 

126947

InChI

InChI=1S/C6H7N3O2/c1-4-2-5(9(10)11)3-8-6(4)7/h2-3H,1H3,(H2,7,8)

InChIKey

JLPYUDJJBGYXEZ-UHFFFAOYSA-N

SMILES

C1(N)=NC=C([N+]([O-])=O)C=C1C

CAS DataBase Reference

18344-51-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-20/21/22-41-22

Safety Statements 

36/37/39-26-22-39-36-37

RIDADR 

UN2811

WGK Germany 

1

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

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

2-Amino-3-methyl-5-nitropyridine Usage And Synthesis

Uses

2-Amino-3-methyl-5-nitropyridine is a pyridine derivative that can be used as a pharmaceutical intermediate.

Chemical Properties

White to yellow crystalline powder.

Synthesis

The general procedure for the synthesis of 2-amino-3-methyl-5-nitropyridine from 2-amino-3-methylpyridine was as follows: 3-methylpyridin-2-amine (5.0 g, 46.2 mmol) was dissolved in concentrated sulfuric acid (24 mL) and the mixture was cooled to 0 °C. At the same time, fuming nitric acid (density = 1.5, 3.5 mL) was cooled to 0 °C. Concentrated sulfuric acid (3.5 mL) was slowly added dropwise to the reaction mixture while keeping the temperature below 20°C. Subsequently, the stirred mixture was gradually warmed to 20 °C and transferred to a second flask in 3-5 mL batches. The second flask was heated to 35-40°C (note: the temperature should not exceed 40°C and the temperature should be carefully monitored after each addition of a new batch). Next, the reaction mixture was continued to be stirred at 50°C for 30 minutes. Once the reaction is complete, the mixture is cooled to room temperature and neutralized with concentrated ammonia. At this point, a precipitate is generated, which is filtered and washed sequentially with water and 50% aqueous DMFA (6 mL). Finally, the product was purified by recrystallization from DMFA to give 3-methyl-5-nitropyridin-2-amine (2.52 g, 35% yield).

References

[1] Patent: EP1894924, 2008, A1. Location in patent: Page/Page column 36
[2] Journal of Organic Chemistry, 1949, vol. 14, p. 328,331
[3] Journal of the American Chemical Society, 1955, vol. 77, p. 3154

2-Amino-3-methyl-5-nitropyridine(18344-51-9)Related Product Information

• Methylparaben
• Kresoxim-methyl
• 4-Methylpyridine
• Bensulfuron methyl
• METSULFURON METHYL
• 2-Amino-3-picoline
• 5-Amino-2-methylpyridine
• 4-Aminopyridine
• 4-Dimethylaminopyridine
• 3-Aminopyridine
• 2-Methyl-5-nitropyridine
• Methyl acetate
• Methyl salicylate
• 2-Chloro-5-chloromethylpyridine
• 2,5-Dimethylpyridine
• 2-Amino-5-nitropyridine
• 2-Amino-3-nitropyridine
• Thiophanate-methyl