39771-28-3

Usage

Uses

Used in Military and Industrial Applications:
2,4,6-Triamino-3,5-dinitropyridine is used as an explosive material in the production of munitions, military equipment, and industrial explosives. Its high stability and resistance to shock and friction make it an ideal component for these applications.
Used in Aerospace Industry:
In the aerospace industry, 2,4,6-Triamino-3,5-dinitropyridine is used as an additive to solid rocket propellants. Its high energy content and low flame temperature contribute to improved performance and safety in rocket propulsion systems.

InChI:InChI=1/C5H6N6O4/c6-1-2(10(12)13)4(7)9-5(8)3(1)11(14)15/h(H6,6,7,8,9)

Upstream product

• 940-06-7 3,5-dinitropyridine 
• 2578-45-2 2-chloro-3,5-dinitropyridine 
• 34981-11-8 2,6-diamino-3,5-dinitropyridine 
• 3073-30-1 3,5-dinitropyridin-2-amine 
• 25194-01-8 4-nitro-2,6-dichloro-pyridine 
• 2587-00-0 2,6-dichloropyridine N-oxide 
• 2402-78-0 2,6-dichloropyridine 
• 650140-90-2 4-amino-2,6-dichloro-3,5-dinitropyridine 
• 2587-02-2 2,6-dichloro-[4]pyridylamine 
• 10425-70-4 4-chloro-3,5-dinitropyridine 
• 31793-29-0 4-Amino-3,5-dinitropyridine 

Downstream Products

• 175553-46-5 2,4,6-triamino-3,5-dinitropyridine-1-oxide 

Relevant academic research and scientific papers

Efficient synthesis of 4-amino-2,6-dichloropyridine and its derivatives

A facile synthetic route to an important intermediate 4-amino-2,6-dichloropyridine was developed. Oxidation of 2,6-dichloropyridine as a starting material gave pyridine N-oxide derivative which was subjected to nitration followed by reduction. Subsequent nitration of the product and nucleophilic displacement reaction were carried out to afford fully substituted energetic pyridine derivatives. Most of the synthetic reactions proceeded under mild conditions.

Aminonitropyridines and their N-oxides

2,6-Diamino-3,5-dinitropyridine 1-oxide has been prepared by mixed acid nitration of 2,6-diaminopyridine, followed by oxidation using hydrogen peroxide in acetic acid. 3,5-Dinitro-2,4,6-triaminopyridine has been prepared by oxidative amination of 2-chloro-3,5-dinitropyridine or 2,6-diamino-3,5-dinitropyridine using potassium permanganate in liquid ammonia, or by "vicarious nucleophilic amination" of 2,6-diamino-3,5-dinitropyridine using hydroxylamine in aqueous potassium hydroxide. 3,5-Dinitro-2,4,6-triaminopyridine 1-oxide has been prepared by oxidation of 3,5-dinitro-2,4,6-triaminopyridine using hydrogen peroxide in acetic acid, and by "vicarious nucleophilic amination" of 2,6-diamino-3,5-dinitropyridine 1-oxide. Nmr spectroscopy and single crystal X-ray diffraction studies have shown that these compounds have the planar structures and intra- and inter-molecular hydrogen bonding necessary to confer on the materials the high density, the thermal and chemical stability, and the explosive insensitivity required for new insensitive energetic materials.

Amination of 3,5-Dinitropyridines with Liquid Ammonia/Potassium Permanganate

3,5-Dinitropyridine and some of its derivatives are aminated with a liquid ammonia solution of potassium permanganate to the corresponding 2-, 4- and 6- mono- and (or) di- and (or) triamino-substituted compounds.The intermediate amino ?-adducts of 3,5-dinitropyridines are detected by 1H-NMR spectroscopy.Quantum-mechanical calculations for a few 3,5-dinitropyridines suggest that the experimentally observed regioselectivity of the amination is a charge-controlled process. Key Words: Amination / Amino ?-adducts / Reactivity indices / Calculations, MNDO / Pyridines

On the Amination of Halogenonitropyridines

Evidence is presented, based on 15N-labeling experiments and 1H NMR spectroscopy, that the conversion of 2-chloro-5-nitropyridine (1) into 2-amino-5-nitropyridine by treatment with potassium amide/liquid ammonia proceeds to about 75percent according to a sequence of reactions involving addition of the amide ion to C-6, ring-opening, and ring-closure N(ANRORC) mechanism>.On the contrary, 2-chloro-3,5-dinitropyridine (11) is nearly quantitatively aminated by liquid ammonia (containing no potassium amide) into 2-amino-3,5-dinitropyridine according to an SN(AE) process, thus no ring-opening being involved.As shown by NMR spectroscopy, the position of addition of liquid ammonia to 11 is temperature dependent.At -60 deg C the addition takes place at C-4, while at -40 deg C the addition at C-6 is strongly favored.Apparently the addition at C-4 is kinetically controlled; the addition at C-6 leads to the thermodynamically more stable adduct.Amination of 11 with liquid ammonia in the presence of potassium permanganate yields mainly 2,6-diamino-3,5-dinitropyridine.