49558-02-3

Basic information

• Product Name: 1,2,5-Oxadiazole,3-methyl-4-nitro-,2-oxide(9CI)
• Synonyms: 1,2,5-Oxadiazole,3-methyl-4-nitro-,2-oxide(9CI)
• CAS NO: 49558-02-3
• Molecular Formula: C₃H₃N₃O₄
• Molecular Weight: 145.07
• Product Categories: NITRO
• Mol File: 49558-02-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 264.14°C (rough estimate)
• Flash Point: 125.7°C
• Appearance: /
• Density: 1.91g/cm³
• Vapor Pressure: 0.00518mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• CAS DataBase Reference: 1,2,5-Oxadiazole,3-methyl-4-nitro-,2-oxide(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,5-Oxadiazole,3-methyl-4-nitro-,2-oxide(9CI)(49558-02-3)
• EPA Substance Registry System: 1,2,5-Oxadiazole,3-methyl-4-nitro-,2-oxide(9CI)(49558-02-3)

Safety Data

• Hazardous Substances Data: 49558-02-3(Hazardous Substances Data)

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

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

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 articles and documents

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.

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