51376-06-8

Basic information

• Product Name: 5-BROMO-2,1,3-BENZOXADIAZOLE
• Synonyms: 5-BROMOBENZO[1,2,5]OXA-DIAZOLE;5-BROMO-2,1,3-BENZOXADIAZOLE;BUTTPARK 85\04-54;2,1,3-Benzoxadiazole,5-bromo-
• CAS NO: 51376-06-8
• Molecular Formula: C₆H₃BrN₂O
• Molecular Weight: 199
• Product Categories: Heterocyclic Building Blocks
• Mol File: 51376-06-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 72 °C
• Boiling Point: 255.778 °C at 760 mmHg
• Flash Point: 108.491 °C
• Appearance: /
• Density: 1.826 g/cm³
• Vapor Pressure: 0.026mmHg at 25°C
• Refractive Index: 1.661
• Storage Temp.: Room temperature.
• PKA: -1.63±0.36(Predicted)
• CAS DataBase Reference: 5-BROMO-2,1,3-BENZOXADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2,1,3-BENZOXADIAZOLE(51376-06-8)
• EPA Substance Registry System: 5-BROMO-2,1,3-BENZOXADIAZOLE(51376-06-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g
• Hazardous Substances Data: 51376-06-8(Hazardous Substances Data)

Usage

General Description

5-Bromo-2,1,3-benzoxadiazole is a chemical compound with the molecular formula C7H4BrN3O. It is a heterocyclic aromatic compound with a bromine atom attached to the benzene ring. 5-BROMO-2,1,3-BENZOXADIAZOLE is commonly used in organic synthesis as a fluorescent labeling reagent and as a building block in the preparation of various pharmaceuticals and agrochemicals. It has also been studied for its potential use in the development of optoelectronic materials such as OLEDs and organic solar cells. 5-Bromo-2,1,3-benzoxadiazole has also shown promise as a fluorogenic probe for the detection of proteins and nucleic acids in biological systems. Due to its versatile applications, this chemical compound has gained attention in the fields of organic chemistry, materials science, and biomedical research.

InChI:InChI=1/C6H3BrN2O/c7-4-1-2-5-6(3-4)9-10-8-5/h1-3H

Upstream product

• 5228-61-5 5-bromo-2-nitroaniline 
• 41153-83-7 6-bromobenzo[c][1,2,5]oxadiazole 1-oxide 
• 847672-84-8 1-azido-4-bromo-2-nitrobenzene 
• 36387-84-5 4-bromo-9-oxido-8-oxa-7,9-diazabicyclo[4.3.0]nona-1⁽⁹⁾,2,4,6-tetraene 
• 88-74-4 2-nitro-aniline 
• 875-51-4 4-Bromo-2-nitroaniline 
• 168297-37-8 4-bromo-2-(tert-butyl-NNO-azoxy)aniline 
• 73686-38-1 4-bromo-[1,2]benzoquinone dioxime 

Downstream Products

• 54286-62-3 benzo[c][1,2,5]oxadiazole-5-carbonitrile 
• 1395071-71-2 5-(4-methoxyphenyl)benzo[c][1,2,5]oxadiazole 
• 1395071-72-3 5-(3-methoxyphenyl)-2,1,3-benzoxadiazole 
• 1395071-74-5 5-(3-cyanophenyl)-2,1,3-benzoxadiazole 
• 1170691-48-1 5-(3-aminophenyl)-2,1,3-benzoxadiazole 
• 1395071-76-7 5-(2,4-difluorophenyl)-2,1,3-benzoxadiazole 
• 1431943-48-4 1-[2-(2,1,3-benzoxadiazol-5-yl)ethyl]-4-[2-(4-nitrophenyl)ethyl]piperazin-2-one 
• 426268-09-9 benzo[c][1,2,5]oxadiazole-5-boronic acid 
• 874-36-2 5-amino-benz[1,2,5]oxadiazole 
• 19155-88-5 benzo[c][1,2,5]oxadiazole-5-carboxylic acid 
• 36389-07-8 benzo[1,2,5]oxadiazole-5-carboxylic acid ethyl ester 
• 59660-58-1 1-(benzo[c][1,2,5]oxadiazol-5-yl)ethan-1-ol 
• 1372151-20-6 5-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)-2,1,3-benzoxadiazole 
• 1428479-63-3 1-{4-(2,1,3-benzoxadiazol-5-ylethynyl)-4-hydroxypiperidin-1-yl}-2-[4-(1H-tetrazol-1-yl)phenyl]ethanone 

Relevant articles and documents

A Common, Facile and Eco-Friendly Method for the Reduction of Nitroarenes, Selective Reduction of Poly-Nitroarenes and Deoxygenation of N-Oxide Containing Heteroarenes Using Elemental Sulfur

A transition metal-free, environment-friendly and practical protocol was developed either for the reduction of nitroarenes or for the deoxygenation of N-oxide containing heteroarenes. The reaction proceeded with the use of a non-toxic and cheap feedstock as elemental sulfur in aqueous methanol under relatively mild conditions. Green chemistry credentials were widely favorable compared to traditional and industrial protocols with good E-factors and a low production of waste. The strategy allowed the efficient reduction of a large variety of substituted-nitroarenes including various o-nitroanilines as well as selective reduction of various poly-nitroarenes in excellent yields with a broad substrate scope. The protocol was successfully extended to the deoxygenation of some N-oxide containing heteroarenes, like benzofuroxans, phenazine N,N'-dioxides, pyridine N-oxides, 2H-indazole N1-oxides, quinoxaline N1,N4-dioxides and benzo[d]imidazole N1,N3-dioxides. A gram-scale example for the synthesis of luminol, in green conditions, was reported. A solid mechanism of reaction was proposed from experimental evidences.

Discovery and development of novel salicylate synthase (MbtI) furanic inhibitors as antitubercular agents

We report on the virtual screening, synthesis, and biological evaluation of new furan derivatives targeting Mycobacterium tuberculosis salicylate synthase (MbtI). A receptor-based virtual screening procedure was applied to screen the Enamine database, identifying two compounds, I and III, endowed with a good enzyme inhibitory activity. Considering the most active compound I as starting point for the development of novel MbtI inhibitors, we obtained new derivatives based on the furan scaffold. Among the SAR performed on this class, compound 1a emerged as the most potent MbtI inhibitor reported to date (Ki = 5.3 μM). Moreover, compound 1a showed a promising antimycobacterial activity (MIC99 = 156 μM), which is conceivably related to mycobactin biosynthesis inhibition.

Furazan-containing bromoarenes in the Suzuki-Miyaura reaction

The palladium-catalyzed cross-coupling reactions of 3-[bromo(het)aryl] furazans and bromobenzofurazans with arylboronic acids afford target biaryls in good yields. 3-Bromo-4-phenylfurazan containing a bromine atom in the furazan ring undergoes decomposition under the reaction conditions.