6-AMINO-3,5-DINITROPYRIDINE Chemical Properties

Melting point:

191-192 °C

Boiling point:

403.1±40.0 °C(Predicted)

Density 

1.694±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

-1.68±0.49(Predicted)

Safety Information

HazardClass 

IRRITANT-HARMFUL

6-AMINO-3,5-DINITROPYRIDINE Usage And Synthesis

Preparation

Ritter202 found that nitration of 2-amino-5-nitropyridine gave the 2-nitrarnino compound and further reaction gave 2-amino-3,5-dinitropyridine.

Uses

3,5-Dinitro-2-pyridinamine can be used to prepare antagonists for NMDA/glycine, AMPA, and Kainate Receptors.

Synthesis

The general procedure for the synthesis of 2-amino-3,5-dinitropyridine from 2-chloro-3,5-dinitropyridine was as follows: 2-chloro-3,5-dinitropyridine (22.3 g, 0.11 mol) was slowly added to a methanol solution of ammonia (7N, 150 mL) in batches at a low temperature of 5-10 °C. The reaction mixture was stirred continuously for 1 h at room temperature and subsequently poured into water (500 mL) to terminate the reaction. The resulting solid product was collected by filtration and washed with cold water (100 mL) to remove impurities. Finally, the product was dried to afford 2-amino-3,5-dinitropyridine (19.55 g, 97% yield), which was used directly in the subsequent reaction without further purification.

References

[1] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 2854 - 2861
[2] Journal of Organic Chemistry, 1985, vol. 50, # 4, p. 484 - 487
[3] Journal of Medicinal Chemistry, 1997, vol. 40, # 22, p. 3679 - 3686
[4] Patent: WO2009/111277, 2009, A1. Location in patent: Page/Page column 53
[5] Patent: US2004/116466, 2004, A1

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