49558-02-3

Usage

Family

Oxadiazole
It belongs to the oxadiazole family, which are heterocyclic compounds containing one oxygen and two nitrogen atoms.

Derivative

1,2,5-Oxadiazole
It is a derivative of 1,2,5-oxadiazole, which is a five-membered ring with two nitrogen atoms and one oxygen atom.

Substituents

Methyl group and nitro group
The compound features a methyl group (-CH3) and a nitro group (-NO2) attached to the oxadiazole ring.

Functional group

Oxide
It has an oxide functional group (-O) in its structure.

Application

Organic chemistry
It is primarily used in the field of organic chemistry as a building block for the synthesis of various pharmaceuticals, agrochemicals, or other organic compounds.

Interest

Chemical and pharmaceutical industries
Due to its unique structure and properties, the compound is of interest to researchers in the chemical and pharmaceutical industries for its potential applications in drug discovery and development.

Registry number

9CI
The compound is identified by the registry number 9CI, which is a unique identifier used in chemical databases and literature.

InChI:InChI=1/C3H3N3O4/c1-2-3(5(7)8)4-10-6(2)9/h1H3

Upstream product

• 498-23-7 citraconic acid 
• 115174-03-3 4-amino-3-methyl-furazan-N-oxide 
• 5570-27-4 4-methyl-3-nitrofuroxan 

Downstream Products

• 63435-83-6 3-(4-fluoro-phenylsulfanyl)-4-methyl-furazan 5-oxide 
• 63435-82-5 3-(4-chloro-phenylsulfanyl)-4-methyl-furazan 5-oxide 
• 63435-81-4 3-methyl-4-p-tolylsulfanyl-furazan 2-oxide 
• 49739-36-8 3-methyl-4-(phenylthio)furoxan 
• 49739-29-9 3-methyl-4-phenoxy-1,2,5-oxadiazole 2-oxide 
• 1198084-45-5 4-benzylthio-3-methylfuroxan 

Relevant academic research and scientific papers

Nitro-, cyano-, and methylfuroxans, and their bis-derivatives: From green primary to melt-cast explosives

In the present work, we studied in detail the thermochemistry, thermal stability, mechanical sensitivity, and detonation performance for 20 nitro-, cyano-, and methyl derivatives of 1,2,5-oxadiazole-2-oxide (furoxan), along with their bis-derivatives. For all species studied, we also determined the reliable values of the gas-phase formation enthalpies using highly accurate multilevel procedures W2-F12 and/or W1-F12 in conjunction with the atomization energy approach and isodesmic reactions with the domain-based local pair natural orbital (DLPNO) modifications of the coupled-cluster techniques. Apart from this, we proposed reliable benchmark values of the formation enthalpies of furoxan and a number of its (azo)bis-derivatives. Additionally, we reported the previously unknown crystal structure of 3-cyano-4-nitrofuroxan. Among the monocyclic compounds, 3-nitro-4-cyclopropyl and dicyano derivatives of furoxan outperformed trinitrotoluene, a benchmark melt-cast explosive, exhibited decent thermal stability (decomposition temperature >200 ?C) and insensitivity to mechanical stimuli while having notable volatility and low melting points. In turn, 4,40-azobis-dicarbamoyl furoxan is proposed as a substitute of pentaerythritol tetranitrate, a benchmark brisant high explosive. Finally, the application prospects of 3,30-azobis-dinitro furoxan, one of the most powerful energetic materials synthesized up to date, are limited due to the tremendously high mechanical sensitivity of this compound. Overall, the investigated derivatives of furoxan comprise multipurpose green energetic materials, including primary, secondary, melt-cast, low-sensitive explosives, and an energetic liquid.

N -Oxide-Controlled Chemoselective Reduction of Nitrofuroxans

A facile and chemoselective SnCl 2 -mediated mild reduction of regioisomeric 3- and 4-nitrofuroxans for the synthesis of aminofurazans and aminofuroxans in good yields is developed. Reduction of 4-nitrofuroxans results in the selective formation of 4-aminofuroxans, while analogous reduction of 3-nitrofuroxans affords 3-aminofurazans as a result of simultaneous reduction of the nitro group and exocyclic N-O bond.

Straightforward Access to the Nitric Oxide Donor Azasydnone Scaffold by Cascade Reactions of Amines

A novel one-pot cascade method for the assembly of valuable NO-donor azasydnone scaffold has been developed. The construction strategy involves a diazotization/azo coupling/elimination/double rearrangement cascade sequence of readily available amines. The

SYNTHESIS AND STRUCTURAL ASSIGNMENT OF BIS(3-METHYLISOXAZOL-5-YL) AND SOME OF ITS DERIVATIVES

By 1H, 13C, 14N, and 15N NMR the structures were established of bis(3-methylisoxazol-5-yl), some of its derivatives, and related compounds, all synthesized for the first time.