16322-23-9

Basic information

• Product Name: 4-nitro-7-(phenylsulfanyl)-2,1,3-benzoxadiazole
• CAS NO: 16322-23-9
• Molecular Formula: C₁₂H₇N₃O₃S
• Molecular Weight: 273.2673
• Mol File: 16322-23-9.mol

Chemical Properties

• Boiling Point: 476.1°C at 760 mmHg
• Flash Point: 241.7°C
• Density: 1.53g/cm³
• Vapor Pressure: 9.03E-09mmHg at 25°C
• Refractive Index: 1.731
• CAS DataBase Reference: 4-nitro-7-(phenylsulfanyl)-2,1,3-benzoxadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-nitro-7-(phenylsulfanyl)-2,1,3-benzoxadiazole(16322-23-9)
• EPA Substance Registry System: 4-nitro-7-(phenylsulfanyl)-2,1,3-benzoxadiazole(16322-23-9)

Safety Data

• Hazardous Substances Data: 16322-23-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Sensing Applications:
4-nitro-7-(phenylsulfanyl)-2,1,3-benzoxadiazole is used as a fluorescent probe for the detection of zinc ions, due to its selective binding affinity for zinc. This makes it a valuable tool in chemical sensing for the identification and quantification of zinc ions in various samples.
Used in Bioimaging Applications:
In the field of bioimaging, 4-nitro-7-(phenylsulfanyl)-2,1,3-benzoxadiazole is utilized as a fluorescence chemosensor for the detection of nitroreductase activity in living cells. Its fluorescent properties allow for the visualization and monitoring of enzyme activity, providing insights into cellular processes and potential applications in disease diagnosis and treatment.
Used in Biomedical Research:
4-nitro-7-(phenylsulfanyl)-2,1,3-benzoxadiazole has potential applications in biomedical research due to its ability to selectively bind to specific biomolecules. This selective binding can be exploited for the development of targeted therapies, drug delivery systems, and other advanced medical technologies.

Upstream product

• 108-98-5 thiophenol 
• 5714-17-0 5-chloro-4-nitrobenzo[c]-[1,2,5]oxadiazole 
• 10199-89-0 NBD chloride 
• 371-42-6 4-Fluorothiophenol 
• 19155-86-3 5-chlorobenzo[c][1,2,5]oxadiazole 
• 1635-61-6 5-chloro-2-nitroaniline 
• 17348-69-5 5-chlorobenzofurazan-1-oxide 
• 35128-56-4 4-bromo-7-nitro-2,1,3-benzoxadiazole 

Downstream Products

• 16597-09-4 7-nitrobenzo[c][1,2,5]oxadiazole-4-thiol 
• 108-98-5 thiophenol 
• 53619-65-1 4-Phenylsulphinyl-7-nitrobenzofurazan 
• 53619-71-9 4-nitro-7-(phenylsulfonyl)benzo[c][1,2,5]oxadiazole 
• 215818-23-8 4-Phenylthio-7-benzoylamino-2,1,3-benzoxadiazole 
• 215818-22-7 4-Phenylthio-7-acetylamino-2,1,3-bemzoxadiazole 
• 215818-24-9 4-Phenylthio-7-amino-2,1,3-benzoxadiazole 

Relevant articles and documents

Colorimetric analysis of malononitrile via the formation of a novel NBD-based CH-acidic dye

Malononitrile is a key starting material used in synthetic organic, medical, and industrial chemistry, but it is also a notorious cyanogenic toxicant. However, selective and sensitive analytical methods for this key chemical are rare. In this research, a

The regulation of biothiol-responsive performance and bioimaging application of benzo[c][1,2,5]oxadiazole dyes

The different oxidation states of sulphur atom play a significant role on functional materials. In this work, a aryl-thioether and its sulphone substituted benzo[c][1,2,5]oxadiazole dyes were synthesized and utilized to determine thiol-containing amino ac

Synthesis and structure-activity relationship of new cytotoxic agents targeting human glutathione-S-transferases

The 6-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)thio)hexan-1-ol (NBDHEX, 1), a "suicide inhibitor" of the glutathione-S-transferase GSTP1-1, showed pro-apoptotic properties in tumor cells, but in vivo studies were limited by poor bioavailability and high af finity towards GSTM2-2, expressed in many noncancerous tissues. Here we describe the synthesis and biological characterization of new 1 analogs (2-40), in which the hydroxyhexyl portion at the C4-sulfur atom has been replaced with phenylcontaining moieties as well as substituted alkyl chains. Some of the new compounds displayed 10-100 times increased water-solubility (8, 11, 17, 26-28, 34, 35), and most of them showed higher GSTP1- 1 selectivity (2-20, 23-26, 31-33, 35) than 1. The presence of a phenyl ring with polar substituents is in general associated, with some exceptions (23, 24) to low cytotoxicity in osteosarcoma U-2OS cells. Differently, some alkyl derivatives possess cytotoxicity comparable (26, 34, 35) or higher (30, 32) than 1. Among the novel compounds, selected ones (26, 27, 34, and 35) deserve further investigation for their anticancer potential.

Development of selective colorimetric probes for hydrogen sulfide based on nucleophilic aromatic substitution

Hydrogen sulfide is an important biological signaling molecule and an important environmental target for detection. A major challenge in developing H2S detection methods is separating the often similar reactivity of thiols and other nucleophiles from H2S. To address this need, the nucleophilic aromatic substitution (SNAr) reaction of H2S with electron-poor aromatic electrophiles was developed as a strategy to separate H2S and thiol reactivity. Treatment of aqueous solutions of nitrobenzofurazan (7-nitro-1,2,3-benzoxadiazole, NBD) thioethers with H 2S resulted in thiol extrusion and formation of nitrobenzofurazan thiol (λmax = 534 nm). This reactivity allows for unwanted thioether products to be converted to the desired nitrobenzofurazan thiol upon reaction with H2S. The scope of the reaction was investigated using a Hammett linear free energy relationship study, and the determined ρ = +0.34 is consistent with the proposed SN2Ar reaction mechanism. The efficacy of the developed probes was demonstrated in buffer and in serum with associated submicromolar detection limits as low as 190 nM (buffer) and 380 nM (serum). Furthermore, the sigmoidal response of nitrobenzofurazan electrophiles with H2S can be fit to accurately quantify H2S. The developed detection strategy offers a manifold for H2S detection that we foresee being applied in various future applications.

Discovery and synthesis of novel benzofurazan derivatives as inhibitors of influenza A virus

The identification of a novel hit compound inhibitor of the protein-protein interaction between the influenza RNA-polymerase PA and PB1 subunits has been accomplished by means of high-throughput screening. A small family of structurally related molecules

Colorimetric signaling of hydrogen sulfide by reduction of a phenylseleno-nitrobenzoxadiazole derivative

A new reaction-based probe for the colorimetric signaling of hydrogen sulfide was developed. Reduction of the nitro group of a nitrobenzoxadiazole moiety to an amino group resulted in pronounced chromogenic signaling in the form of a yellow to pink color change. The transformation of the nitro group to amino group was confirmed by the 1H NMR spectroscopy. The seleno derivative showed more efficient signaling behavior than the phenylthio and phenoxy analogues. Hydrogen sulfide signaling of phenylseleno- nitrobenzoxadiazole probe was fast and completed immediately after sample preparation. Selective signaling of hydrogen sulfide was possible in the presence of commonly encountered metal ions and anions with a detection limit of 2.1 × 10-6 M.

Effects of the substituent groups at the 4- and 7-positions on the fluorescence characteristics of benzofurazan compounds

To develop new fluorogenic reagents having the benzofurazan structure, we investigated the effects of the substituent groups at the 4- and 7-positions of the benzofurazan skeleton on the fluorescence characteristics (fluorescence intensity, maximum excitation wavelength and maximum emission wavelength). Seventy benzofurazan compounds substituted at the 4- and 7-positions were obtained for this purpose. The Hammett substituent constant (σp) was adopted as a parameter for electronic effects by substituent groups. The study using the sum and the difference of the Hammett substituent constants (σp) at the 4- and 7-positions revealed that the highly fluorescent benzofurazan compounds were classified into two groups and that singlet excitation energies, calculated by the maximum excitation and emission wavelengths, of the benzofurazan compounds were different between these two groups. The fluorescence characteristics of benzofurazan compounds substituted at the 4- and 7-positions were empirically predictable by these relationships and σp values. A new fluorogenic reagent, 4-phenylaminosulfonyl-7-fluoro-2,1,3-benzoxadiazole, for amines was developed based on this method and applied to the amino acids analysis.

Reactivity of 7-Halogeno-4-nitrobenzofurazans towards Thiophenols. A Kinetic Investigation

The reactions of 7-chloro- and 7-bromo-4-nitrobenzofurazan with thiophenols in methanol afford the products of arylthiodehalogenation together with the corresponding hydrogen halide.Kinetic analysis indicates a remarkable auto-inhibition which has been in