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

Melting point:

174-176°C

Boiling point:

329.0±37.0 °C(Predicted)

Density 

1.596±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Soluble in dimethyl formamide, dimethyl sulfoxide, hot ethanol, ethyl acetate and hot methanol.

pka

1.31±0.47(Predicted)

form 

Solid

color 

Yellow

InChI

InChI=1S/C5H4ClN3O2/c6-3-1-2-8-5(7)4(3)9(10)11/h1-2H,(H2,7,8)

InChIKey

DIRINUVNYFAWQF-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2933399990

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

Description

It is usually used as the intermediate or raw material in organic synthesis and pharmaceutical industry. Specifically, this chemical can act as the intermediate in the synthesis of 5-amino-azaoxindole derivatives.¹ Moreover, this substance may be involved in the preparation of pharmaceutically active compounds that can be used in the treatment of proliferative disorders, as well as other diseases or conditions in which aurora kinase and/or FLT3 activity is implicated.² In addition, this chemical has been demonstrated to function as the intermediate in the synthesis of 1-deaza-6-methylthiopurine ribonucleoside, which is proved to exhibit cytotoxicty.³ Besides, 2-amino-4-chloro-3-nitropyridine can be utilized to fabricate central nervous system (CNS) active compounds.⁴

Reference

1. Tzvetkov, N. T.; Muller, C. E., Facile synthesis of 5-aminoand 7-amino-6-azaoxindole derivatives. Tetrahedron Lett. 2012, 53, 5597-5601.
2. Julian Blagg; Bavetsias; Moore; Linardopoulos, pharmaceutically active compounds. US Patent US 9447092 B2 2016.
3. JMontgomery, J. A.; Hewson, K., 1-DEAZA-6-METHYLTHIOPURINE RIBONUCLEOSIDE. J. Med. Chem. 1966, 9, 354-+.
4. JHarry Louis Yale; Sheehan, J. T., CNS active compounds US Patent 4022897 1977.

Chemical Properties

Bright Yellow Needles

Uses

2-Amino-4-chloro-3-nitropyridine is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.

Synthesis

4-Chloro-2-aminopyridine (6.4 g, 50 mmol) was slowly added dropwise to fuming nitric acid (50 mL) under ice bath cooling conditions. The reaction mixture was gradually warmed to room temperature and then poured into water containing crushed ice to quench the reaction. The precipitate was collected by filtration and purified by fast column chromatography (eluent: dichloromethane/methanol = 100:1, v/v) to afford 2-amino-3-nitro-4-chloropyridine as a white solid (7.4 g, 85% yield).

References

[1] Patent: CN106146504, 2016, A. Location in patent: Paragraph 0168; 0169; 0170; 0171; 0172
[2] Patent: KR101556826, 2015, B1. Location in patent: Paragraph 0065-0067
[3] ChemMedChem, 2012, vol. 7, # 6, p. 1057 - 1070
[4] Patent: US2008/51404, 2008, A1. Location in patent: Page/Page column 110
[5] Patent: US2016/96834, 2016, A1. Location in patent: Paragraph 0244

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