34981-11-8

Usage

Uses

Used in Energetic Materials Industry:
2,6-Diamino-3,5-dinitropyridine is used as a key component in the formulation of energetic materials, specifically for the creation of less sensitive, more environmentally friendly explosives. Its high-nitrogen content and explosive properties contribute to the performance and safety of these materials.
Used in Research and Development:
DADNP is utilized in research and development settings to study the properties and behavior of high-nitrogen compounds, particularly in the context of their potential applications in energetic materials. This research can lead to the discovery of new, safer, and more efficient materials for various industries.

InChI:InChI=1/C5H5N5O4/c6-4-2(9(11)12)1-3(10(13)14)5(7)8-4/h1H,(H4,6,7,8)/p+1

Upstream product

• 940-06-7 3,5-dinitropyridine 
• 3073-30-1 3,5-dinitropyridin-2-amine 
• 2578-45-2 2-chloro-3,5-dinitropyridine 
• 141-86-6 2.6-diaminopyridine 
• 1158646-15-1 2,6-diamino-3-nitropyridine-5-sulfonic acid 

Downstream Products

• 39771-28-3 2,4,6-triamino-3,5-dinitropyridine 
• 132683-64-8 2,6-diamino-3,5-dinitropyridine-1-oxide 
• 175553-46-5 2,4,6-triamino-3,5-dinitropyridine-1-oxide 
• 38926-45-3 2,3,5,6-tetraaminopyridine 

Relevant academic research and scientific papers

A simple and efficient route for preparing 2,3,5,6-tetraaminopyridine hydrochloride salt

A simple and efficient route for preparing 2,3,5,6-tetraaminopyridine hydrochloride salt (TAP-3HCl.H2O) was introduced in this paper. The title compound was synthesized, as usual, in two steps (nitration and hydrogenation) with a total yield of

Diimidazo[4,5-b:4′,5′-e]pyridine: synthesis and nucleophilic aromatic substitution reaction

1,7-Dihydrodiimidazo[4,5-b:4′,5′-e]pyridine obtained by reductive heterocyclization was N-arylated with 4-fluoronitrobenzene to form two regioisomers in 7: 3 ratio. This N-arylation is considered as a model reaction for the polymer synthesis.

Nitration method for preparing 2, 6-diamido-3, 5-binitro pyridine by ultrafine zeolite-based micro-channel reaction

The invention provides a nitration method for preparing 2, 6-diamido-3, 5-binitro pyridine by ultrafine zeolite-based micro-channel reaction. The nitration method includes the steps: heating and uniformly mixing crushed sodium amide, decahydronaphthalene and p-toluidine, performing microwave heating reaction on mixture and pyridine by a Y-shaped micro-channel reactor, and filtering and recrystallizing the mixture and the pyridine to obtain 2, 6-diamido pyridine; blowing ultrafine HZSM-5 catalysts into an outlet channel of the Y-shaped micro-channel reactor, placing the modified Y-shaped micro-channel reactor into an ice-water bath, leading the 2, 6-diamido pyridine and dichloromethane solution containing nitrogen pentoxide into the Y-shaped micro-channel reactor, accelerating flow and rapidly increasing temperature to reach reaction temperature to obtain a 2, 6-diamido-3, 5-binitro pyridine crude product; secondarily recrystallizing, filtering and drying the 2, 6-diamido-3, 5-binitro pyridine crude product, adding the crude product into distilled water, boiling the distilled water and performing dimethyl sulfoxide secondary crystallization to obtain the 2, 6-diamido-3, 5-binitro pyridine with high yield and purity.

Synthesis of diaminodinitropyridine

A process for the preparation of diaminodinitropyridine or diaminodinitrobenzene by contacting an aminopyridine or aminobenzene with oleum and nitric acid, wherein the improvement comprises adding at least about 1% molar excess of nitric acid, based upon

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.

Synthesis and Reactions of Dinitrated Amino and Diaminopyridines

Nitration of amino- and diaminopyridines and -picolines led, in unexpected one-step reactions, to dinitrated derivatives.Dinitropicolines gave styrylpiridines, and 2-amino-6-hydroxy-3,5-dinitropyridine was transformed by the thermolysis of its azido deriv

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.