17348-69-5

Basic information

• Product Name: 5-CHLOROBENZOFUROXAN
• Synonyms: 5-CHLOROBENZOFUROXAN;5-CHLORO-2,1,3-BENZOXADIAZOL-1-IUM-1-OLATE;5-Chlorobenzfurazan1-oxide;5-Chloro-beznofurazan oxide;5-Chloro-2,1,3-benzoxadiazole-1-ium-1-olate;5-chloro-1-oxidanidyl-2,1,3-benzoxadiazol-1-ium;5-chloro-1-oxido-2,1,3-benzoxadiazol-1-ium;5-chloro-1-oxido-benzofurazan-1-ium
• CAS NO: 17348-69-5
• Molecular Formula: C₆H₃ClN₂O₂
• Molecular Weight: 170.55
• Mol File: 17348-69-5.mol

Chemical Properties

• Melting Point: 45-48°C
• Boiling Point: 287.1°Cat760mmHg
• Flash Point: 127.4°C
• Appearance: /
• Density: 1.69g/cm³
• Vapor Pressure: 0.00438mmHg at 25°C
• Refractive Index: 1.701
• CAS DataBase Reference: 5-CHLOROBENZOFUROXAN(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLOROBENZOFUROXAN(17348-69-5)
• EPA Substance Registry System: 5-CHLOROBENZOFUROXAN(17348-69-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 17348-69-5(Hazardous Substances Data)

Usage

Uses

Used in Energetic Materials Development:
5-Chlorobenzofuroxan is utilized as a high-energy density material, contributing to the advancement of energetic materials due to its inherent properties that make it suitable for applications requiring high energy release.
Used in Pharmaceutical Synthesis:
As a precursor, 5-Chlorobenzofuroxan plays a crucial role in the synthesis of compounds with potential pharmaceutical applications, aiding in the development of new drugs and therapeutic agents.
Used in Research:
In the field of scientific research, 5-Chlorobenzofuroxan is employed as a research tool, particularly in the study of nitric oxide metabolism, providing insights into biological processes and potential therapeutic interventions.
Used in Therapeutic Applications:
5-Chlorobenzofuroxan is explored as a potential therapeutic agent for the treatment of various diseases, leveraging its chemical properties to target specific conditions and improve patient outcomes.
Used in Safety and Handling Protocols:
Given its explosive properties, 5-Chlorobenzofuroxan necessitates the establishment of proper handling and storage protocols to ensure the safety of personnel and equipment in industrial and research settings.

InChI:InChI=1/C6H3ClN2O2/c7-4-1-2-6-5(3-4)8-11-9(6)10/h1-3H

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Relevant articles and documents

Synthesis and characterization of newly fused 1,2-dihydropyrido[3,4-b], bridged oxadiazol-2-yl, 4-substituted-benzylidene hydrazide and arylidene 6-chloroquinoxaline 1,4-dioxides

Some simple reactions using commercially available chemicals were used in the preparation of new biologically remarkable quinoxaline 1,4-dioxide derivatives. Several steps performed on 4-chloro-2-nitroaniline resulted in a quinoxaline 1,4-dioxide derivati

Effect of complexation of 3-aminoquinoxaline-2-carbonitrile 1,4-dioxides with palladium and copper on their anti-T. cruzi activity

Pd(II) and Cu(II) complexes of 3-aminoquinoxaline-2-carbonitrile 1,4-dioxides were prepared in order to improve the anti-Trypanosoma cruzi activity of these ligands. The in vitro evaluations demonstrated that the metal complexation modified the activity of the ligands in different manners. Except for one compound, complexation with palladium increased the trypanosomicidal activity 20-80-times. Besides, copper also modified favorably the activity, however, the copper compounds resulted less active than the palladium ones, at the studied doses. Springer Science+Business Media, LLC 2011.

Straightforward one-pot synthesis of benzofuroxans from o-halonitrobenzenes in ionic liquids

Treatment of o-halonitrobenzenes with sodium azide in a [empyrr][BF4]/Bu4NBr/H2O system gives benzofuroxans in high yields, with the recovery and reuse of the ionic liquid for at least ten times.

Discovery of 1,2,3-triazole based quinoxaline-1,4-di-N-oxide derivatives as potential anti-tubercular agents

A series of thirty one novel 2-(((1-(substituted phenyl)-1H-1,2,3-triazol-4-yl)methoxy)carbonyl)-3-methylquinoxaline-1,4-dioxide (7a-l), 3-(((1-(substituted phenyl)-1H-1,2,3-triazol-4-yl)methoxy)carbonyl)-6-chloro-2-methylquinoxaline-1,4-dioxide (8a-l) and 2-(((1-(substituted phenyl)-1H-1,2,3-triazol-4-yl)methoxy)carbonyl)-6,7-dichloro-3-methylquinoxaline-1,4-dioxide (9a-g) analogues were synthesized, characterized using various analytical techniques and single crystal was developed for the compounds 8 g and 9f. Synthesized compounds were evaluated for in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv strain and two clinical isolates Spec. 210 and Spec. 192. The titled compounds exhibited minimum inhibitory concentration (MIC) ranging from 30.35 to 252.00 μM. Among the tested compounds, 8e, 8 l, 9c and 9d exhibited moderate activity (MIC = 47.6 – 52.0 μM) and 8a exhibited significant anti-tubercular activity (MIC = 30.35 μM). Furthermore, 8e, 8 l, and 9d were found to be less toxic against human embryonic kidney, HEK 293 cell lines. Finally, a docking study was also performed using MTB DNA Gyrase (PDB ID: 5BS8) for the significantly active compound 8a to know the exact binding pattern within the active site of the target enzyme.

Cu-Catalyzed π-Core Evolution of Benzoxadiazoles with Diaryliodonium Salts for Regioselective Synthesis of Phenazine Scaffolds

The Cu-catalyzed regioselective synthesis of phenazine N-oxides was realized from benzoxadiazoles and diaryliodonium salts. The process was initiated by the electrophilic arylation of benzoxadiazoles with diaryliodonium salts and followed by benzocyclization reactions. The further reduction of N-oxides in situ to phenazine scaffolds and deviation to organic fluorescent materials were readily accomplished.

Hypoxia-Selective Agents Derived from Quinoxaline 1,4-Di-N-oxides

Hypoxic cells, which are a common feature of solid tumors, but not normal tissues, are resistant to both anticancer drugs and radiation therapy.Thus the identification of drugs with selective toxicity toward hypoxic cells is an important objective in anticancer chemotherapy.The benzotriazine di-N-oxide (SR 4233, Tirapazamine) has been shown to be an efficient and selective cytotoxin for hypoxic cells.Since the bioreductive activation of Tirapazamine is thought to be due to the presence of the 1,4-di-N-oxide moiety, a series of 3-aminoquinoxaline-2-carbonitrile 1,4-di-N-oxides with a range of electron-donating and -withdrawing substituents in the 6- and /or 7- positions has been synthesized and evaluated for toxicity to hypoxic cells.Electrochemical studies of the quinoxaline di-N-oxides and Tirapazamine showed that as the electron-withdrawing nature of the 6(7)-substituent increases, the reduction potential becomes more positive and the compound is more readily reduced.Apart from the unsubstituted 6a and the 6,7-dimethyl derivative 6c, the quinoxaline di-N-oxide have reduction potentials significantly more positive than Tirapazamine (Epc -0.90 V).The most potent cytotoxins to cells in culture were the 6,7-dichloro and 6,7-difluoro derivatives 6i and 6l, which were 30-fold more potent than Tirapazamine.The 6(7)-fluoro and 6(7)-chloro compounds, 6e and 6h, showed the greatest hypoxia selectivity.Four of the compounds, 6e, 6f, 6h and 6i, killed the inner cells of multicellular tumor spheroids in vitro.In vivo Balb/c mice tolerated a dose of these four compounds twice the size of that of Tirapazamine.This study demonstrates that quinoxaline 1,4-di-N-oxides could provide useful hypoxia-selective therapeutic agents.

Pyrolysis of Aryl Azides. VII. Interpretation of Hammett Correlations of Rates of Pyrolysis of Substituted 2-Nitroazidobenzenes

Rates and products of pyrolysis have been obtained for ten 2-nitroazidobenzenes with 4- or 5-substituents.Rate data at 100 deg C are correlated with Hammett constants of the 4- and 5-substituents, with respect to both the azido (A) and nitro (N) reaction