2-Amino-3-nitro-4-picoline Chemical Properties

Melting point:

136-140 °C(lit.)

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

form 

Crystalline Powder

pka

2.97±0.47(Predicted)

color 

Yellow

BRN 

139111

InChI

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

InChIKey

IKMZGACFMXZAAT-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

6635-86-5(CAS DataBase Reference)

NIST Chemistry Reference

Pyridine, 2-amino-3-nitro-4-methyl-(6635-86-5)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-36/37/39-22

WGK Germany 

3

F 

10

HazardClass 

IRRITANT

HS Code 

29333999

MSDS

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

2-Amino-3-nitro-4-picoline Usage And Synthesis

Chemical Properties

light yellow crystal powder

Uses

2-Amino-4-methyl-3-nitropyridine was used in the synthesis of 2-amino-5-hydroxy-4-methyl-3-nitropyridine, 2-amino-4-hydroxymethyl-3-nitropyridine and 2-amino-4-methyl-3-nitropyridine-1-oxide by undergoing biotransformation by Cunninghamella elegans ATCC 26269.

General Description

The crystal structure of 2-amino-4-methyl-3-nitropyridine was elucidated.

Synthesis

The general procedure for the synthesis of 2-amino-4-methyl-5-nitropyridine and 4-methyl-3-nitropyridin-2-amine from 2-amino-4-methylpyridine was carried out as follows: commercially available 2-amino-4-methylpyridine (Fluka, purity >99%) was used as starting material according to the method previously described by Talik and Talik [29]. This was done as follows: 25 g of 2-amino-4-methylpyridine was dissolved in 125 cm3 concentrated sulfuric acid (Fluka, 96%). The reaction mixture was cooled to 0°C under strong stirring by adding ice mixed with sodium chloride. Subsequently, 37.5 cm3 of nitric acid (Chempur, 65%, density = 1.4 g/cm3) was slowly added, keeping the reaction temperature below 10°C. The reaction mixture was stirred under continuous cooling for 1.5 hours, followed by standing at room temperature for 1 hour. Next, the reaction mixture was sequentially heated in a water bath at 40°C for half an hour, at 60-70°C for 1 hour and in a boiling water bath for half an hour. After completion of the reaction, the mixture was cooled to room temperature, poured into ice water and adjusted to a weakly basic pH with ammonia. the solid product was collected by vacuum filtration. Steam distillation was utilized to separate the two nitro isomers (3-nitro and 5-nitro isomers). The more volatile 3-nitro isomer (I) was first distilled and concentrated and dried to give the pure product (10 g). The residual 5-nitro isomer (III) was collected by filtration and recrystallized from water (initial addition of sulfuric acid and activated carbon to dissolve the compound and remove impurities). After neutralization, filtration and drying, about 15 g of 5-nitroisomer (III) was obtained. 2-Amino-4-methyl-3,5-dinitropyridine (II) was prepared from 2-amino-4-methyl-5-nitropyridine (III) using a similar method (nitration and rearrangement to dinitropyridine). The residue was purified by crystallization in water to give 2-amino-4-methyl-3-nitropyridine (I) (yield: 27%, 10 g, melting point 134 °C), 2-amino-4-methyl-3,5-dinitropyridine (II) (yield: 80%, 10.4 g, melting point 197 °C) and 2-amino-4-methyl-5-nitropyridine (III) (yield: 40%, 15 g (yield: 40%, 15g, melting point 218°C). Melting points were determined using a K?fler apparatus and the chemical composition of the compounds was verified by Carlo Erba Analyzer (model 1104).

References

[1] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2012, vol. 96, p. 952 - 962
[2] Journal of the Chemical Society, 1954, p. 2448,2455
[3] Journal of the American Chemical Society, 1955, vol. 77, p. 3154
[4] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
[5] Journal of Molecular Structure, 2013, vol. 1043, p. 15 - 27

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