38858-89-8

Usage

Uses

Used in Explosives and Propellants Industry:
3,5-dinitro-1H-pyrazole is used as a high-energy density material for its significant heat of explosion and stability, which are critical for the performance of explosives and propellants. Its properties allow for the creation of more powerful and efficient devices within this industry.
Used in Organic Synthesis:
3,5-dinitro-1H-pyrazole serves as a building block in the synthesis of other organic compounds, contributing to the development of new chemical entities for various applications across different industries.
Used as a Chemical Reaction Reagent:
In the realm of chemical research and development, 3,5-dinitro-1H-pyrazole is utilized as a reagent to facilitate specific chemical reactions, enabling the production of desired products with greater efficiency and selectivity.

InChI:InChI=1/C3H2N4O4/c8-6(9)2-1-3(5-4-2)7(10)11/h1H,(H,4,5)

Upstream product

• 38858-81-0 1,3-dinitro-1H-pyrazole 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 32683-48-0 1-methyl-3,5-dinitro-1H-pyrazole 
• 1241916-18-6 (4-fluorophenyl)(4-(5-methoxy-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone 

Relevant academic research and scientific papers

Lithium Nitropyrazolates as Potential Red Pyrotechnic Colorants

Strontium-based red pyrotechnic colorants have fallen into disrepute due to the harmful influence of this alkaline earth metal on adolescents. In this context, the energetic character, safety, and combustion to benign nitrogen gas of nitropyrazoles are used for the design of the corresponding lithiated materials, which are investigated as potential replacements in the current work. For this purpose, the lithium salts of 3,4-dinitro-1H-pyrazole, 3,5-dinitro-1H-pyrazole, 4-amino-3,5-dinitro-1H-pyrazole, 3,4,5-trinitro-1H-pyrazole, and 4-hydroxy-3,5-dinitro-1H-pyrazole were extensively characterized by standard analytical methods, low-temperature single-crystal X-ray diffraction, studies of the thermo-chemical behavior, and sensitivity assessments. Our assumption that the high nitrogen contents and the low oxygen balances of these compounds would adjust a cool, reductive flame atmosphere essential for red emissions by lithium was put to the test.

METHOD FOR PREPARING NITROPYRAZOLES

A process for the sigmatropic rearrangement of the compound of formula in which R3 is an NO2 group and R4 is either a hydrogen or an NO2 group, includes heat treating the compound by microwave.

Isomers of Dinitropyrazoles: Synthesis, Comparison and Tuning of their Physicochemical Properties

Three isomeric dinitropyrazoles (DNPs) were synthesized starting from readily available 1H-pyrazole by slightly improved methods than described in the literature. 3,4-Dinitropyrazole (3), 1,3-dinitropyrazole (4), and 3,5-dinitropyrazole (5) were obtained and compared to each other with respect to thermal stability, crystallography, sensitivity and energetic performance. Two isomers (3 and 4) show high densities (1.79 and 1.76 g cm–3) and interesting thermal behavior as melt-castable materials (3: Tmelt.=71 °C, Tdec.=285 °C; 5: Tmelt. = 68 °C, Tdec.=171 °C). Furthermore, eight salts (sodium, potassium, ammonium, hydrazinium, hydroxylammonium, guanidinium, aminoguanidinium and 3,6,7-triamino-[1,2,4]triazolo[4,3-b][1,2,4]triazole (TATOT) of 3 and 5 were synthesized in order to tune performance and sensitivity values. These compounds were characterized using 1H, 13C, 14N, 15N NMR and IR spectroscopy as well as mass spectrometry, elemental analysis and thermal analysis through differential scanning calorimetry. Crystal structures of 14 compounds were obtained (3–7, 10–12 and 15–20) by low-temperature single crystal X-ray diffraction. Impact, friction and electrostatic discharge (ESD) values were also determined by standard methods. The sensitivity values range between 8.5 and 40 J for impact and 240 N and 360 N for friction and show mainly insensitive character. The energetic performances were determined using recalculated X-ray densities, heats of formation and the EXPLO5 code and support the energetic character of the title compounds. The calculated energetic performances (VD: 6245–8610 m s?1; pCJ: 14.1–30.8 GPa) were compared to RDX ((O2NNCH2)3).

Synthesis of 4-substituted pyrazole-3,5-diamines: Via Suzuki-Miyaura coupling and iron-catalyzed reduction

A general and efficient synthesis of 4-substituted-1H-pyrazole-3,5-diamines was developed to access derivatives with an aryl, heteroaryl, or styryl group, which are otherwise relatively difficult to prepare. The first step is based on the Suzuki-Miyaura cross-coupling reaction utilizing the XPhos Pd G2 precatalyst. The coupling reactions of 4-bromo-3,5-dinitro-1H-pyrazole with the electron-rich/deficient or sterically demanding boronic acids enabled the production of the corresponding dinitropyrazoles. The subsequent iron-catalyzed reduction of both nitro groups with hydrazine hydrate accomplished the synthesis. The additional demethylation of the 4-methoxystyryl derivative allowed the production of the carboanalog of CAN508 reported as a selective CDK9 inhibitor.

COMPOUNDS AND METHODS FOR KINASE MODULATION, AND INDICATIONS THEREFOR

Compounds of Formula (I) or a pharmaceutically acceptable salt, a solvate, a tautomer, an isomer or a deuterated analog thereof, wherein A, J, R1, R2, R3, R4, R5, R6, R7, R9, X, m and n are as described herein, compositions thereof, and methods and uses thereof.

High-selectivity and high-yield non-solvent preparation method of 1-methyl-3,4,5-trinitropyrazole (MTNP) intermediate 3,5-dinitropyrazole

The invention provides a high-selectivity and high-yield non-solvent preparation method of a high-energy insensitive explosive 1-methyl-3,4,5-trinitropyrazole (MTNP) intermediate 3,5-dinitropyrazole. The synthesis method comprises the steps: with pyrazole as a starting material, carrying out nitrification to introduce N-NO2 to a 1 site, and carrying out non-solvent rearrangement reaction translocation to a 3 site to generate C-NO2; then introducing N-NO2 into the 1 site, carrying out non-solvent rearrangement reaction translocation to a 5 site to generate C-NO2, to obtain the intermediate 3,5-dinitropyrazole, and carrying out nitration and methylation to obtain MTNP which is an ideal candidate for substitution of TNT. The synthesis method is simple, high in selectivity and high in yield, the used non-solvent rearrangement method is an important way for solving environmental pollution, the use of some high-toxic organic solvents is avoided, the cost is reduced, the problem of tedious post-processing is solved, and the requirements of green chemistry are met.

Synthetic method for 1-methyl-3,4,5-triaminopyrazole

The invention relates to a synthetic method for a compound, especially to a s ynthetic method for 1-methyl-3,4,5-triaminopyrazole. The method uses 3-nitropyrazole as a raw material and prepares the target product through the following steps: nitration, thermal rearrangement, nitration, ammonification and methylation. The method has mild reaction conditions and high yield.

Metal salts of dinitro-, trinitropyrazole, and trinitroimidazole

The syntheses of alkali and earth alkaline dinitropyrazolate (DNP), trinitropyrazolate (TNP), and trinitroimidazolate (TNI) salts are reported. Additionally, copper trinitroimidazolate was synthesized. Their characterization by NMR spectroscopy, mass spectrometry, elemental analysis, and vibrational spectroscopy is reported as well. Crystal structures of compound Ba(DNP)2 (9), which crystallizes with one molecule of methanol and ethyl ether as well as of compounds Sr(TNP)2·3H2O (12), Ba(TNP)2·3H2O (13), and LiTNI·3H2O (14) were determined. The energetic and thermal properties were measured as well. Green- and red-burning pyrotechnic formulations containing barium salts 9 and 13 as well as strontium salts 8 and 12 serving as colorants are tested. Additionally, formulations using Sr(TNP)2·3H2O (12) and Ba(TNP)2·3H2O (13) as the oxidizer and colorant at the same time were examined. The formulations were investigated with regard to their combustion behavior and performances such as burn time, dominant wavelength, spectral purity, luminous intensity, and luminous efficiency. The sensitivities towards ignition stimuli and the decomposition temperatures were determined as well.

Four syntheses of 4-Amino-3,5-dinitropyrazole

In this paper, syntheses of 4-amino-3,5-dinitropyrazole from four different starting materials are described. The starting materials were 4-nitropyrazole, 4-nitro-3,5-dimethylpyrazole, 3,5-dinitropyrazole, and 4-chloropyrazole, respectively. They are compared in terms of yield, number of steps and suitability for scale-up into pilot scale production. The overall yield, calculated from commercially available starting materials, ranged from 21% in the case of synthesis via 3,5-dinitropyrazole up to 61% for the one starting from 4-chloropyrazole. With numerous factors taken into account, the latter was chosen for a pilot scale study and the product could be produced in batches of 200 g.

QUINOLINE AND ISOQUINOLINE COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are compounds for treatment of JAK kinase mediated diseases, including JAK2 kinase-, JAK3 kinase- or TYK2 kinase-mediated diseases. Also provided are pharmaceutical compositions comprising the compounds and methods of using the compounds a