13490-32-9

Usage

Uses

Used in Pharmaceutical Industry:
4-AMINO-3-FURAZANECARBOXAMIDOXIME is used as a key intermediate for the preparation of inhibitors of indoleamine 2,3-dioxygenase (IDO). These inhibitors play a crucial role in modulating the immune response and have potential applications in the treatment of various diseases, including cancer and autoimmune disorders.
Additionally, 4-AMINO-3-FURAZANECARBOXAMIDOXIME is used in the synthesis of 3-azolylpropanohydroxamic acids, which serve as procollagen C-proteinase inhibitors. These inhibitors are essential in the regulation of the extracellular matrix and have potential therapeutic applications in the treatment of fibrosis and other connective tissue disorders.

InChI:InChI=1/C3H5N5O2/c4-2(6-9)1-3(5)8-10-7-1/h9H,(H2,4,6)(H2,5,8)

Upstream product

• 17376-59-9 1,3-diamino-1,2,3-trihydroximinopropane 
• 109-77-3 malononitrile 
• 36568-05-5 2-(hydroxyimino)malononitrile 
• 7803-49-8 hydroxylamine 
• 156463-85-3 3-amino-1,2,5-oxadiazole-4-carbonitrile 
• 120493-19-8 3-(4-aminofurazan-3-yl)-5-trifluoromethyl-1,2,4-oxadiazole 
• 163011-64-1 4-aminofurazan-3-carboxyamid-O-acetyloxime 

Downstream Products

• 13300-88-4 4-amino-1,2,5-oxadiazole-3-carboxylic acid amide 
• 17376-66-8 7-Oxo-6.7-dihydro-furazano<3.4-d>pyrimidin 
• 129206-52-6 3-(3-Amino-4-furazanyl)-5-phenyl-1,2,4-oxadiazole 
• 163011-64-1 4-aminofurazan-3-carboxyamid-O-acetyloxime 
• 163011-56-1 4-(1,2,4-oxadiazol-3-yl)furazan-3-amine 
• 164363-81-9 3-amino-4-(5-methyl-1,2,4-oxadiazol-3-yl)furazan 
• 147085-13-0 4-amino-N-hydroxy-1,2,5-oxadiazole-3-carboximidamidoyl chloride 
• 156463-85-3 3-amino-1,2,5-oxadiazole-4-carbonitrile 
• 296244-55-8 3,4-bis(4-amino-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole N-oxide 
• 120493-19-8 3-(4-aminofurazan-3-yl)-5-trifluoromethyl-1,2,4-oxadiazole 

Relevant academic research and scientific papers

A furazan-fused pyrazole N-oxide via unusual cyclization

6-Nitro-pyrazolo[3,4-c]furazanate 5-oxide, a new fused anion with high energy, was designed and synthesized via an unusual intramolecular cyclization reaction of 3 by using a mixture of 100% nitric acid and trifluoroacetic anhydride followed by KI reduction. The potassium (6) and nitrogen-rich energetic (9-16) salts were prepared, and fully characterized by IR and multinuclear NMR spectroscopy, elemental analysis, and single-crystal X-ray structuring, 6, 9 and 16. Hydroxylammonium salt (10) has excellent detonation performance but high sensitivity, while 13 and 16 have detonation velocities comparable to 1,3,5-trinitro-1,3,5-triazinane (RDX), which suggests they may have potential application as green primary or secondary explosives.

A new coordination compound based on 4-amino-3-(tetrazol-5-yl)-furazan (HAFT): preparation, crystal structure, and thermal properties

The green nitrogen-rich coordination compound Cd(SCZ)2(AFT)2 (1) (AFT =4-amino-3-(5-tetrazolate)-furazan and SCZ = semicarbazide) was first synthesized and characterized by EA and Fourier Transform Infrared (FT-IR). The single crystal was cultivated and determined with X-ray diffraction. It revealed that 1 crystallizes in the monoclinic space group P21/c. A Cd2+ ion is coordinated by four N atoms and two O atoms to form a distorted octahedral structure. Among them, two nitrogen atoms are from the two AFT ions and the other four atoms are from two SCZ molecules. The thermal decomposition behavior of 1 was studied with DSC and TG-DTG methods. The apparent activation energy (E), thermal stability, and safety parameters (TSADT, TTIT, and Tb) were calculated for 1. Moreover, entropy of activation (ΔS≠), enthalpy of activation (ΔH≠), free energy of activation (ΔG≠), specific heat capacity (Cp), and impact sensitivity were also discussed in detail.

Nitramino-functionalized tetracyclic oxadiazoles as energetic materials with high performance and high stability: crystal structures and energetic properties

A series of tetracyclic energetic materials were developed through the introduction of 1,2,4-oxadiazole into nitramino-1,2,5-oxadiazole. All these thirteen new compounds were fully characterized and seven of them were further confirmed by single crystal X-ray diffraction. Salt formation led to planarization of the parent structure, reduction in lengths, increase in bond-dissociation energies of N-NO2 bonds, and formation of hydrogen bonds, which significantly increased decomposition temperatures from 84 °C (the neutral compound) to 187-303 °C (the energetic salts). Thus, the increase in thermal stability falls in the range of 103-219 °C. To the best of our knowledge, 219 °C is the largest reported increase in thermal stability due to salt formation. In addition, electrostatic surface potentials and noncovalent interactions (π-π stacking) were analyzed to understand structure-property relationships of these compounds. Both theoretical calculations and practical explosive experiments indicate that the dihydroxylammonium salt exhibits better detonation performance than the powerful explosive RDX. The tetracyclic backbone provides these compounds with enhanced stability. Short synthesis steps, low cost, good thermostability, excellent detonation performance, and acceptable mechanical sensitivity highlight the practical applications of these energetic compounds.

A new method for the synthesis of nitriles enriched with the 15N isotope

A new synthetic method for the preparation of 15N-labeled nitriles from nonlabeled nitriles is proposed. - Key words: 15N isotope; nitriles; amidoximes.

Synthesis, crystal structure, and thermal properties of Ni(NH3)4(AFT)2

Ni(NH3)4(AFT)2 [NiC6H16N18O2, AFT = 4-amino-3-(5-tetrazolate)furazan] is synthesized and characterized by elemental analysis and Fourier-transform infrared spectroscopy for the first time. X-ray diffraction measurements are used to determine the crystal structure of compound 1. The results demonstrate that compound 1 crystallized in the orthorhombic crystal system. The nickel(II) ion is six-coordinated by N atoms from two AFT-ligands and four NH3 molecules. Its thermal properties are investigated by differential scanning calorimetry and thermogravimetry-derivative thermogravimetry methods, with the results demonstrating that the differential scanning calorimetry curve exhibits two endothermic and one exothermic processes. The endothermic processes are in the range of 130–510 °C with a peak temperature of 188 °C. The temperature from 230 to 400 °C is the exothermic process in which the peak temperature is 314.58 °C. In addition, Kissinger’s and Ozawa-Doyle’s methods are used for calculating the non-isothermal kinetics parameters. Moreover, the apparent activation energy (E), safety, and thermal stability parameters (TSADT, TTIT, Tb) for Ni(NH3)4(AFT)2 are calculated. In addition, the calculated thermodynamic functions (?S≠, ?H≠, and ?G≠) for the exothermic decomposition process of Ni(NH3)4(AFT)2 are 55.07 J mol?1 K?1, 196.18 kJ mol?1, and 164.90 kJ mol?1, respectively.

Assembly of Nitrofurazan and Nitrofuroxan Frameworks for High-Performance Energetic Materials

The design of novel energetic materials with improved performance, optimized parameters, and environmental compatibility remains a challenging task. In this study, new high-energy materials based on isomeric dinitrobi-1,2,5-oxadiazole structures comprising nitrofurazan and nitrofuroxan subunits were synthesized. Due to planarity and strong noncovalent interactions, these materials display high density values as determined by single-crystal X-ray diffraction. The thermal, impact, and friction sensitivities of both isomers are similar to that of nitroesters. Their high detonation performance along with the combined benefits of high density, high heat of formation, and good oxygen balance make the synthesized compounds promising as explosives and highly-energetic oxidizers.

Design, synthesis, and biological evaluation of 1,2,5-oxadiazole-3-carboximidamide derivatives as novel indoleamine-2,3-dioxygenase 1 inhibitors

Indoleamine 2,3-dioxygenase 1 (IDO1) is the enzyme catalyzing the oxidative metabolism of tryptophan, which accounts for cancer immunosuppression in tumor microenvironment. Several compounds targeting IDO1 have been reported and epacadostat shows strong i

1,3,4-Oxadiazole Bridges: A Strategy to Improve Energetics at the Molecular Level

Many energetic materials synthesized to date have limited applications because of low thermal and/or mechanical stability. This limitation can be overcome by introducing structural modifications such as a bridging group. In this study, a series of 1,3,4-oxadiazole-bridged furazans was prepared. Their structures were confirmed by 1H and 13C NMR, infrared, elemental, and X-ray crystallographic analyses. The thermal stability, friction sensitivity, impact sensitivity, detonation velocity, and detonation pressure were evaluated. The hydroxylammonium salt 8 has an excellent detonation performance (D=9101 m s?1, P=37.9 GPa) and insensitive properties (IS=17.4 J, FS=330 N), which show its great potential as a high-performance insensitive explosive. Using quantum computation and crystal structure analysis, the effect of the introduction of the 1,3,4-oxadiazole moiety on molecular reactivity and the difference between the sensitivities and thermal stabilities of mono- and bis-1,3,4-oxadiazole bridges are considered. The synthetic method for introducing 1,3,4-oxadiazole and the systematic study of 1,3,4-oxadiazole-bridged compounds provide a theoretical basis for future energetics design.

Synthesis of furazane conjugated new heterocycles

An improved route for the synthesis of 3-(4-aminofurazane-3-yl)-1,2,4-oxadiazole heterocycles using micro-wave irradiation is reported. The preparation of novel 4-(thiazol-4-yl)furazan-3-ylamine, 4-(pyrimidin-4-yl)furazan-3-ylamine and, 4-(pyrazolidin-3-yl)furazan-3-ylamine heterocycles are described.

1D energetic metal–organic frameworks assembled with energetic combination of furazan and tetrazole

Two novel 1D Cd(II) energetic MOFs [Cd(NH2NH2)(AFT)2·0.7H2O]n (1) and [Cd(ODH)1.5(AFT)2·5H2O]n (2), combining the advantages of tetrazole-ring and furazan-ring, were successfully synthesized based on 2D energetic MOF [Cd(H2O)2(AFT)2]n (3, AFT = 4-amino-3-(5-tetrazolate)-furazan, ODH[dbnd]NH2NHCOCONHNH2[dbnd]oxalyl-dihydrazide). The crystal structures were determined by single-crystal X-ray diffraction, and fully characterized by elemental analysis and FT-IR spectroscopy. The thermal stability and impact sensitivity were also investigated. For 1, 1D energetic MOF had an outstanding thermal stability (Tp > 300 °C) and insensitivity (IS > 24.5 J). In addition, the non-isothermal kinetics parameters, critical temperature of thermal explosion, entropy of activation, enthalpy of activation and free energy of activation were discussed in detail. For 2, it was revealed that the each Cd(II) cation is located in a unique hepta-coordination environment. Noticeably, tetrazole-ring of AFT group presents typical monodentate coordination mode, and ODH molecule presents typical tridentate and tetradentate coordination modes, featuring a one-dimensional chain structure. Therefore, the reasonable assembly strategy plays a decisive role in energetic properties of MOF-based energetic materials.