14531-55-6

Basic information

• Product Name: 3,5-Dimethyl-4-nitro-1H-pyrazole
• Synonyms: ART-CHEM-BB B001468;AKOS 90439;AKOS B001468;4-NITRO-3,5-DIMETHYL-1H-PYRAZOLE;3,5-DIMETHYL-4-NITRO-1H-PYRAZOLE;TIMTEC-BB SBB009217;5-23-05-00160 (Beilstein Handbook Reference);1H-Pyrazole,3,5-dimethyl-4-nitro-(9CI)
• CAS NO: 14531-55-6
• Molecular Formula: C₅H₇N₃O₂
• Molecular Weight: 141.13
• Product Categories: NITRO
• Mol File: 14531-55-6.mol
• Article Data: 25

Chemical Properties

• Melting Point: 125.0 to 129.0 °C
• Boiling Point: 325°C(lit.)
• Flash Point: 138 °C
• Appearance: /
• Density: 1.339 g/cm³
• Vapor Pressure: 0.00157mmHg at 25°C
• Refractive Index: 1.578
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.75±0.50(Predicted)
• CAS DataBase Reference: 3,5-Dimethyl-4-nitro-1H-pyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dimethyl-4-nitro-1H-pyrazole(14531-55-6)
• EPA Substance Registry System: 3,5-Dimethyl-4-nitro-1H-pyrazole(14531-55-6)

Safety Data

• RTECS: UQ6585000
• HazardClass: IRRITANT
• Hazardous Substances Data: 14531-55-6(Hazardous Substances Data)

Usage

General Description

3,5-Dimethyl-4-nitro-1H-pyrazole is a chemical compound with the formula C6H7N3O2. It is a yellow crystalline solid that is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. 3,5-Dimethyl-4-nitro-1H-pyrazole is also known for its potent explosive properties and is often used as a precursor in the manufacturing of energetic materials. Additionally, 3,5-Dimethyl-4-nitro-1H-pyrazole has been studied for its potential use as a high-energy propellant and is being researched for its applications in fuel systems and pyrotechnics. Due to its explosive nature and potential hazards, this compound should be handled and stored with caution in a controlled laboratory environment.

InChI:InChI=1/C5H7N3O2/c1-3-5(8(9)10)4(2)7-6-3/h1-2H3,(H,6,7)

Upstream product

• 67-51-6 3,5-dimethyl-1H-pyrazole 
• 1122-04-9 3,5-dimethyl-4-nitrosopyrazole 
• 1123-49-5 3,5-dimethyl-4-nitroisoxazole 
• 70951-87-0 1-nitro-3,5-dimethylpyrazole 
• 3656-06-2 (E)-3,5-dimethyl-4-(p-tolyldiazenyl)-1H-pyrazole 
• 592-56-3 acetaldazine 
• 29917-12-2 Isonitrosoacetylacetone 
• 2033-45-6 4-iodo-3,5-dimethyl-1H-pyrazole 
• 72950-51-7 F₂BCH₃COCOCCH₃NO₂ 
• 956477-62-6 N-difluoromethyl-3,5-dimethylpyrazole 
• 123-54-6 acetylacetone 
• 64-19-7 acetic acid 
• 7697-37-2 nitric acid 
• 7664-93-9 sulfuric acid 

Downstream Products

• 74245-84-4 5-(3,5-Dimethyl-4-nitro-pyrazol-1-yl)-1-methyl-3-nitro-1H-[1,2,4]triazole 
• 22244-55-9 1-methyl-3-nitro-1,2,4-triazol-5-one 
• 302542-44-5 2-(3,5-dimethyl-4-nitro-pyrazol-1-yl)-N-o-tolyl-acetamide 
• 89352-55-6 trans-Ir(PPh₃)2(CO)(3,5-dimethyl-4-nitropyrazolate) 
• 82887-94-3 Pt(dppe)(3,5-dimethyl-4-nitropyrazole)2 
• 5809-38-1 3,5-dimethyl-4-nitro-1-phenyl-1H-pyrazole 
• 1315322-80-5 3,5-dimethyl-1-(4-methylphenyl)-4-nitro-1H-pyrazole 
• 5920-56-9 2-(4-amino-3,5-dimethyl-pyrazol-1-yl)-ethanol 
• 1394162-46-9 N-(1-(2-hydroxyethyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide 
• 1170237-93-0 1,4-bis((4-nitro-3,5-dimethyl-1H-pyrazol-1-yl)methyl)benzene 
• 1458554-46-5 N-(phenyl)-2-(3,5-dimethyl-4-nitro-1H-pyrazol-1-yl)acetamide 

Relevant articles and documents

Silica-sulfuric acid catalyzed nitrodeiodination of iodopyrazoles

We report here the synthesis of nitropyrazoles in good to excellent yields from iodopyrazoles over silica-sulfuric acid catalyst for the first time. The present procedure require less acid, offers a simplified workup procedure, and may be applied for the

An antiferromagnetic metalloring pyrazolate (Pz) framework with [Cu12(μ2-OH)12(Pz)12] nodes for separation of C2H2/CH4 mixture

The search for functional metalloring organic frameworks (MROFs) has been of continuous interest in the fields of both molecular rings and metal-organic frameworks (MOFs) due to their importance in many multifunctional applications. Herein, a hierarchical pyrazolate framework MROF-12 with the topology of the Schl?fli symbol {460.66} is reported, which is constructed by an elongated rigid ligand and attractive metalloring cluster nodes [Cu12(μ2-OH)12(Pz)12]. MROF-12 not only adopts the unique functionalities of the metalloring clusters but also inherits the porous properties of MOFs. The large [Cu12(μ2-OH)12(Pz)12] metalloring nodes with the diameter of 12.202 ? endow MROF-12 with excellent stability and antiferromagnetism, and they are bridged by linear pyrazolate ligands (H2NDI) to form micro-mesoporous MROF with permanent porosity. The activated sample MROF-12a can exhibit a relatively high Brunauer-Emmett-Teller/Langmuir surface area (460.7/571.9 m2 g-1) as well as pore volume of 0.240 cm3 g-1. Dynamic fixed bed breakthrough experiments indicate that the separation of C2H2/CH4 or CO2/CH4 mixtures can be efficiently achieved through a column packed with MROF-12a solid.

Synthesis of high-performance insensitive energetic materials based on nitropyrazole and 1,2,4-Triazole

A new family of symmetric (4-nitro-1H-pyrazole-3,5-diyl)bis(1H-1,2,4-Triazole)-based derivatives were obtained. All these new compounds were characterized by (1H, 13C)NMR spectroscopy, infrared spectroscopy, elemental analysis and differential scanning calorimetry (DSC). The structures of 5,5′-(4-nitro-1H-pyrazole-3,5-diyl)bis(3-nitro-1H-1,2,4-Triazole) (6) and N,N′-((4-nitro-1H-pyrazole-3,5-diyl)bis(1H-1,2,4-Triazole-5,3-diyl))dinitramide (7) were further confirmed by single crystal X-ray diffraction. In addition, the theoretical calculations by using the Gaussian 09 package show that target compounds have high heats of formation ranging from 1.40 to 2.84 kJ g-1. Among them, the safety and detonation performances of 6 (D: 8747 m s-1, P: 33.0 GPa, Td: 238.2 °C, IS: 30 J) and energetic salts dihydroxylammonium((4-nitro-1H-pyrazole-3,5-diyl)bis(1H-1,2,4-Triazole-5,3-diyl))bis(nitroamide) (9) (D: 9077 m s-1, P: 33.6 GPa, IS: >40 J) and dihydrazinium((4-nitro-1H-pyrazole-3,5-diyl)bis(1H-1,2,4-Triazole-5,3-diyl))bis(nitroamide) (10) (D: 8759 m s-1, P: 30.2 GPa, IS: >40 J) are comparable to those of 1,3,5-Trinitroperhydro-1,3,5-Triazine (RDX: D = 8795 m s-1, P = 34.9 GPa, Td = 210 °C, IS: 7.4 J) due to the positive effect of ternary hydrogen bonds.

Energetic Tricyclic Polynitropyrazole and Its Salts: Proton-Locking Effect of Guanidium Cations

An axisymmetric polynitro-pyrazole molecule, 3,5-di(3,5-dinitropyrazol-4-yl)]-4-nitro-1H-pyrazole (5), and its salts (6-12) were prepared and fully characterized. These compounds not only show promising energetic properties but also show a unique tautomeric switch via combining different cations with the axisymmetric compound (5). Its salts (6-9) remain axisymmetric when the cations are potassium, ammonium, or amino-1,2,4-triazolium. However, when the cations are guanidiums, the salts (10-12) dramatically become asymmetric owing to the fixed proton. The introduction of guanidium cations breaks the tautomeric equilibrium by blocking the prototropic transformations and results in the switch-off effect to tautomerism. The structural constraints of 1H NMR and 13C NMR spectra provide strong evidence for the unusual structural constraint phenomenon. These stabilized asymmetric tautomers are very important from the point of molecular recognition, and this research may promote further developments in synthetic and isolation methodologies for novel bioactive pyrazole-based compounds.

Faujasite catalyzed nitrodeiodination of iodopyrazoles

Nitrodeiodination of iodopyrazoles using nitric acid/Faujasite has been investigated. The present procedure is simple, rapid and convenient and requires no sulfuric acid or oleum and may be applied for the synthesis of several nitropyrazoles in good yield

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.

Based on triazole nitrogen heterocyclic energetic compounds and their synthesis methods

The present invention discloses a triazole-based nitrogen heterocyclic energy-containing compound and a method of synthesis thereof. The energetic compound is 4-nitro-3,5-bis(3,4-diamino-1,2,4-triazole-5-yl) 1H- pyrazole. By the synthesis method of the present invention synthesized based on the actual measurement of impact sensitivity of triazole nitrogen heterocyclic energetic compounds >40J, friction sensitivity > 360N, calculated burst velocity of 8197m/s, The burst pressure is 24.2Gpa, the thermal decomposition temperature is 318.6 °C, the performance is better than TNT, the thermal decomposition temperature and sensitivity are better than RDX, and it is stable at room temperature, and its synthesis method is simple, the synthesis process is safe and controllable, it can achieve mass production, and its thermal decomposition temperature is high, and it has application prospects in the field of heat-resistant explosives.