10199-91-4

Basic information

• Product Name: 4-AMINO-7-NITRO-2,1,3-BENZOXADIAZOLE
• Synonyms: AURORA KA-525;4-AMINO-7-NITRO-2,1,3-BENZOXADIAZOLE;4-AMINO-7-NITROBENZOFURAZANE;TIMTEC-BB SBB001500;4-Nitro-2,1,3-benzooxadiazole-7-amine;4-Nitrobenzofurazane-7-amine;7-Nitro-2,1,3-benzoxadiazole-4-amine
• CAS NO: 10199-91-4
• Molecular Formula: C₆H₄N₄O₃
• Molecular Weight: 180.12
• Mol File: 10199-91-4.mol

Chemical Properties

• Boiling Point: 445.6°C at 760 mmHg
• Flash Point: 223.3°C
• Appearance: /
• Density: 1.684g/cm³
• Vapor Pressure: 3.88E-08mmHg at 25°C
• Refractive Index: 1.745
• CAS DataBase Reference: 4-AMINO-7-NITRO-2,1,3-BENZOXADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-7-NITRO-2,1,3-BENZOXADIAZOLE(10199-91-4)
• EPA Substance Registry System: 4-AMINO-7-NITRO-2,1,3-BENZOXADIAZOLE(10199-91-4)

Safety Data

• Hazardous Substances Data: 10199-91-4(Hazardous Substances Data)

Usage

Uses

Used in Biomedical Applications:
4-AMINO-7-NITRO-2,1,3-BENZOXADIAZOLE is used as a fast responsive photo-switchable dual-color fluorescent in cyclodextrin nanogels for cancer cell imaging. Its ability to switch between two different fluorescent states upon exposure to light makes it a valuable tool for visualizing and studying cancer cells, potentially aiding in the development of targeted therapies and early detection methods.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-AMINO-7-NITRO-2,1,3-BENZOXADIAZOLE may be utilized as a building block or intermediate in the synthesis of various drug molecules. Its unique structure and properties could contribute to the development of novel therapeutic agents with specific targeting capabilities or improved pharmacokinetic profiles.
Used in Chemical Research:
4-AMINO-7-NITRO-2,1,3-BENZOXADIAZOLE can also be employed in chemical research as a model compound for studying the properties and reactivity of benzoxadiazole derivatives. This may lead to a better understanding of the structure-activity relationships in this class of compounds and facilitate the design of new molecules with desired properties for various applications.
Used in Material Science:
The photo-switchable properties of 4-AMINO-7-NITRO-2,1,3-BENZOXADIAZOLE make it a candidate for use in the development of advanced materials with potential applications in optoelectronics, sensors, and other technology-driven fields. Its ability to change its fluorescence properties upon light exposure could be harnessed to create responsive materials with tailored functionalities.

InChI:InChI=1/C6H4N4O3/c7-3-1-2-4(10(11)12)6-5(3)8-13-9-6/h1-2H,7H2

Upstream product

• 1336-21-6 ammonium hydroxide 
• 10199-89-0 NBD chloride 
• 106-45-6 para-thiocresol 
• 68-12-2 N,N-dimethyl-formamide 
• 67-68-5 dimethyl sulfoxide 
• 78949-95-8 (3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-[(2S)-1-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]propan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol 
• 101237-25-6 N-(4-Hydroxyphenyl)-4-amino-7-nitrobenz-2,1,3-oxadiazol 
• 1035440-44-8 C₁₂H₆N₄O₄ 
• 1849-36-1 para-nitrobenzenethiol 
• 106-54-7 p-Chlorothiophenol 
• 108-98-5 thiophenol 
• 696-63-9 4-Methoxybenzenethiol 
• 7116-16-7 4-chloro-2,1,3-benzoxadiazole 
• 19155-86-3 5-chlorobenzo[c][1,2,5]oxadiazole 

Downstream Products

• 88955-90-2 7-(N-tosyl-L-phenylalanyl)amino-4-nitrobenzo-2-oxa-1,3-diazole 
• 89784-51-0 7-(N-mesyl-L-phenylalanyl)amino-4-nitrobenzo-2-oxa-1,3-diazole 
• 1579947-08-2 4-((tert-butyldimethylsilyl)oxy)benzyl (7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)carbamate 
• 215860-46-1 4,7-Diamino-2,1,3-benzoxadiazole 
• 21123-74-0 4-amino-5,7-dinitrobenzofurazan 

Relevant articles and documents

An NBD–NH2 fluorescent probe for bioimaging: existence of a specific detection of ClO?

Abstract: A fluorescent probe 4-amino-7-nitrobenz-2-oxa-1,3-diazole NBD–NH2 for critical sensing hypochlorous (ClO?) has been developed in this paper. Probe NBD–NH2 exhibited excellent sensitivity and high selectivity toward detection of ClO? in CH3CH2OH/HEPES solution (1:4, v/v, 10?mM, pH 7.4), where the detection limit as low as 40?nM. The green fluorescence of NBD–NH2 was distinctly quenched by addition of ClO?. In addition, the new probe was also applied for bioimaging using HeLa cells and exist a critical detection of ClO? in living cells. Graphical abstract: [Figure not available: see fulltext.].

An NBD fluorophore-based colorimetric and fluorescent chemosensor for hydrogen sulfide and its application for bioimaging

Hydrogen sulfide (H2S) is an important gaseous mediator in cellular physiology and pathology. For understanding the biological action of H2S to both healthy and disease states, it is important to develop H2S-selective sensor. Herein we report a colorimetric and fluorescent probe, which employs an NBD moiety as fluorophore, and is equipped with azide group as H2S-active unit. The probe exhibits selective and sensitive response to H2S in aqueous solution. By employing 1 mM sensor, the detection limit was evaluated to be 680 nM with a signal-to-noise ratio of 3. Confocal microscopy imaging experiments demonstrate the probe has potential as a powerful tool for the imaging of hydrogen sulfide in living cells. Crown Copyright

Pyrimidine-based fluorescent COX-2 inhibitors: Synthesis and biological evaluation

The cyclooxygenase-2 (COX-2) enzyme is overexpressed in a variety of cancers and mediates inflammatory processes that aid the growth and progression of malignancies. Three novel and selective fluorescent COX-2 inhibitors have been designed and synthesized on the basis of previously reported pyrimidine-based COX-2 inhibitors and the 7-nitrobenzofurazan fluorophore. In vitro evaluation of COX-1/COX-2 isozyme inhibition identified N-(2-((7-nitro-benzo[c][1,2,5]oxadiazol-4-yl)amino)propyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoro-methyl)-pyrimidin-2-amine (6) as a novel potent and selective COX-2 inhibitor (IC50 = 1.8 μM). Lead compound (6) was further evaluated for its ability to selectively visualize COX-2 isozyme in COX-2 expressing human colon cancer cell line HCA-7 using confocal microscopy experiments.

Fluorescent sensory microparticles that "light-up" consisting of a silica core and a molecularly imprinted polymer (MIP) shell

From darkness came light: Incorporation of urea-based fluorescent dyes in an anion-imprinted thin polymer shell coated onto silica microparticles leads to a unique and highly enantioselective fluorescent "light-up" response to analytes (see scheme, MIP molecularly imprinted polymer). Copyright

Anion-induced urea deprotonation

The urea-based receptor 1 (l-(7-nitrobenzo[l,2,5]oxadiazol-4-yl)3-(4- nitrophenyl)urea, L-H), interacts with X ions in MeCN, according to two consecutive steps: 1) formation of a hydrogen-bond complex [L-H...X] -; 2) deprotonation of L-H to giv

Photophysical and dynamic NMR studies on 4-amino-7-nitrobenz-2-oxa-1, 3-diazole derivatives: Elucidation of the nonradiative deactivation pathway

A series of 4-aminonitrobenzoxadiazole (NBD) derivatives in which the amino nitrogen is part of a four- to seven-membered heterocyclic ring and a second series of 4-dialkylamino NBD derivatives with different alkyl chain lengths have been prepared and fully characterized and their photophysical properties investigated in an attempt to find out the nonradiative deactivation pathway of the fluorescent state in these systems. It is observed that the fluorescence properties of the NBD derivatives are highly sensitive to the structure of the amino moiety and the polarity of the surrounding media. It is shown that the nonradiative rate constants for the derivatives with large alkyl groups and large ring systems are considerably higher than those for systems with smaller alkyl groups and smaller ring systems. Dynamic NMR experiments have been carried out to probe the internal motion in the systems. The internal rotation around the bond connecting the amino nitrogen and the NBD ring is found to be rather slow in the ground state. The rate for the internal rotation is found to be the highest for the six-membered ring, and this has been interpreted in terms of the partial double bond character of the C-N bond. The results of the experiments seem to indicate that inversion of the amino nitrogen plays the most important role in determining the fluorescence efficiency of the systems.

Cd2+-triggered amide tautomerization produces a highly Cd2+-selective fluorescent sensor across a wide pH range

An NBD-derived fluorescent sensor termed CdTS was reported to sense Cd2+ with very high binding selectivity and significant fluorescence turn-on signal selectivity (65 fold enhancement). The amide/di-2-picolylamine receptor binds Cd2+ in an imidic acid tautomeric form, but binds most of other metal ions in an amide tautomeric form. The transformable ability makes CdTS have the specific selectivity for Cd2+. Additionally, CdTS can fluoresently and colorimetricly recognize Cd2+ across a wide pH range from 4.5 to 11.5. Finally, we applied CdTS to detect Cd2+ in living cells.

Fluorophore-labeled cyclooxygenase-2 inhibitors for the imaging of cyclooxygenase-2 overexpression in cancer: Synthesis and biological studies

A group of cyclooxygenase-2 (COX-2)-specific fluorescent cancer biomarkers were synthesized by linking the anti-inflammatory drugs ibuprofen, (S)-naproxen, and celecoxib to the 7-nitrobenzofurazan (NBD) fluorophore. In vitro COX-1/COX-2 inhibition studies

Turn-on fluorescent probe designed for fluoride ion sensing in aqueous media

Abstract A NBD-based probe for selective detection of fluoride ion in aqueous media is reported. The probe was designed by applying rules for water solubility and membrane permeability. The probe functions through the fluoride mediated cascade reaction which was studied by 1H NMR, HPLC analysis, UV-vis, and fluorescence spectroscopy. The sensing process was marked by a colour change from colourless to yellow, and an intriguing 120-fold turn-on green fluorescence. Application of the probe for selective detection of fluoride was demonstrated by live-cell imaging.

22-NBD-cholesterol as a novel fluorescent substrate for cholesterol-converting oxidoreductases

Docking simulations and experimental data indicate that 22-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-23,24-bisnor-5-cholen-3β- ol (22-NBD-cholesterol), a common fluorescent sterol analog, binds into active sites of bovine cytochrome P450scc and microbial cholesterol dehydrogenases (CHDHs) and then undergoes regiospecific oxidations by these enzymes. The P450scc-dependent system was established to realize N-dealkylation activity toward 22-NBD-cholesterol, resulting in 7-nitrobenz[c][1,2,5]oxadiazole-4-amine (NBD-NH2) formation as a dominant fluorescent product. Basing on LC-MS data of the probes derivatized with hydroxylamine or cholesterol oxidase, both pregnenolone and 20-formyl-pregn-5-en-3β-ol were deduced to be steroidal co-products of NBD-NH2, indicating intricate character of the reaction. Products of CHDH-mediated conversions of 22-NBD-cholesterol were defined as 3-oxo-4-en and 3-oxo-5-en derivatives of the steroid. Moreover, the 3-oxo-4-en derivative was also found to be formed after 22-NBD-cholesterol incubation with pathogenic bacterium Pseudomonas aeruginosa, indicating a possible application of the reaction for a selective and sensitive detection of some microbes. The 3-keto-4-en derivative of 22-NBD-cholesterol may be also suitable as a new fluorescent probe for steroid hormone-binding enzymes or receptors.