1516-58-1

Basic information

• Product Name: 2-nitrophenyl azide
• Synonyms: 2-nitrophenyl azide;1-Azido-2-nitrobenzene;1-Nitro-2-azidobenzene
• CAS NO: 1516-58-1
• Molecular Formula: C₆H₄N₄O₂
• Molecular Weight: 0
• Mol File: 1516-58-1.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 2-nitrophenyl azide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-nitrophenyl azide(1516-58-1)
• EPA Substance Registry System: 2-nitrophenyl azide(1516-58-1)

Safety Data

• Hazardous Substances Data: 1516-58-1(Hazardous Substances Data)

Usage

Uses

Used in Bioconjugation and Affinity Labeling Studies:
2-nitrophenyl azide is used as a photolabile crosslinker for the study of biomolecular interactions. It is particularly instrumental in photoaffinity labeling experiments, where it helps elucidate the structural and functional aspects of protein-protein and receptor-ligand interactions.
Used in Photoaffinity Labeling Experiments:
In this application, 2-nitrophenyl azide serves as a reactive intermediate that, upon exposure to ultraviolet light, forms a highly reactive nitrene. This nitrene can covalently bind to nearby biomolecules, allowing researchers to probe and map the interactions and binding sites with high specificity.
Used in the Development of Photoactive Surfaces:
2-nitrophenyl azide is utilized in creating surfaces that can immobilize biomolecules. The photoreactive nature of the compound allows for the controlled attachment of biological molecules to surfaces, which is crucial for applications such as biosensors and biochips.
Used in the Synthesis of Photoreactive Polymers:
In the field of materials science, 2-nitrophenyl azide is used in the synthesis of polymers that have photoreactive properties. These polymers are advantageous in drug delivery systems and biomaterials, where the ability to control the release or interaction of biologically active compounds through light exposure is beneficial.
Used in Drug Delivery Systems and Biomaterials:
2-nitrophenyl azide contributes to the advancement of drug delivery systems by enabling the development of polymers that can release their payload in response to light stimuli. This feature is particularly useful in targeted drug delivery and tissue engineering applications, where spatial and temporal control over the release of bioactive molecules is required.

InChI:InChI=1/C6H5N4O2/c7-9-8-5-3-1-2-4-6(5)10(11)12/h1-4,7H/q+1

Upstream product

• 54495-98-6 O-Benzoylhydroxylamine 
• 119-66-4 2-nitrobenzenediazonium chloride 
• 88-74-4 2-nitro-aniline 
• 612-29-3 o-nitronitrosobenzene 
• 17603-82-6 isopropyl-N-fluorocarbamate 
• 365-33-3 2-nitrobenzenediazonium tetrafluoroborate 
• 3034-19-3 (2-nitrophenyl)hydrazine 
• 302-01-2 hydrazine 
• 1493-27-2 ortho-nitrofluorobenzene 
• 552-32-9 o-nitroacetanilide 
• 103-84-4 Acetanilid 
• 577-19-5 2-nitrophenyl bromide 
• 25910-37-6 2-Nitrophenyldiazonium 
• 609-73-4 o-nitroiodobenzene 

Downstream Products

• 480-96-6 benzofurazan oxide 
• 15866-38-3 3-phenyl-benzo[e][1,2,3]triazolo[5,1-c][1,2,4]triazine 5-oxide 
• 65961-04-8 7a-morpholin-4-yl-1-(2-nitro-phenyl)-(3ar,7ac)-1,3a,4,6,7,7a-hexahydro-thiopyrano[3,4-d][1,2,3]triazole 
• 40468-63-1 (2-nitro-phenyl)-(1,2,5-triphenyl-1H-1λ⁵-phosphol-1-ylidene)-amine 
• 93-58-3 benzoic acid methyl ester 
• 7418-32-8 N-(2-nitrophenyl)formamide 
• 88-74-4 2-nitro-aniline 
• 145326-29-0 [1-Morpholin-4-yl-2-phenyl-eth-(E)-ylidene]-(2-nitro-phenyl)-amine 
• 149179-59-9 4,5-Dihydro-4,4-dimethyl-5-morpholino-1-(2-nitrophenyl)-1,2,3-triazole 
• 145326-21-2 4-[(4R,5S)-5-Methyl-3-(2-nitro-phenyl)-4,5-dihydro-3H-[1,2,3]triazol-4-yl]-morpholine 
• 145326-19-8 4-[(4R,5S)-5-Ethyl-3-(2-nitro-phenyl)-4,5-dihydro-3H-[1,2,3]triazol-4-yl]-morpholine 
• 145326-22-3 7a-Morpholin-4-yl-1-(2-nitro-phenyl)-3a,4,5,6,7,7a-hexahydro-1H-benzotriazole 
• 145326-20-1 [(4S,5R)-5-Ethyl-3-(2-nitro-phenyl)-4,5-dihydro-3H-[1,2,3]triazol-4-yl]-dimethyl-amine 
• 51849-78-6 2,3,4r,5-tetraphenyl-3,4-dihydro-2H-[1,2,3]diazaphosphole 3c-oxide 

Relevant articles and documents

Revisiting the thermal decomposition of five ortho-substituted phenyl azides by calorimetric techniques

The thermal decomposition (TD) of 2-azidophenylmethanol (1), 2-azidobenzenecarbaldehyde (2), 1-(2-azidophenyl)-1-ethanone (3), (2-azidophenyl)(phenyl)methanone (4) and 1-azido-2-nitrobenzene (5) was analysed by DSC, TG and C80 calorimetric techniques under both oxidative and non-oxidative conditions. The TD of these azides in solution is well known to give the corresponding benzoxazoles, generally in good yields, with the exception of azide 1. When both the outcomes from the solid phase and in 'solution phase' TD reactions combined with the results from EI-MS experiments were considered, sufficient information was available to estimate the azides intrinsic molecular reactivity (MIR).

Design, synthesis and antifungal activity of novel indole derivatives linked with the 1,2,3-triazole moiety via the CuAAC click reaction

A series of novel indole derivatives linked with the 1,2,3-triazole moiety was designed, synthesised by the CuCl2/Zn-catalysed Huisgen cycloaddition and characterised. The antifungal activity of all the prepared compounds against Colletotrichum capsici and cotton Physalospora pathogens was evaluated and the results indicated that these compounds showed inhibitory effect for fungi and the inhibition ratio of the best was up to 83.3%. The preliminary structure-activity relationship is also discussed in this paper.

Synthesis and antimicrobial potential of nitrofuran-triazole congeners

A series of 5-nitrofuran-triazole congeners were designed and synthesized by carrying out suitable structural modifications of the previously reported counterparts and were evaluated for their antimicrobial potential against both Gram-positive and Gram-ne

Synthesis of aryl azides via post-cleavage modification of polymer-bound triazenes

Starting from immobilized arenes on the triazene T1 linker resin, cleavage was achieved by trifluoroacetic acid in the presence of trimethylsilyl azide to obtain aryl azides in good yields and excellent purities. A novel cleavage protocol has been introduced and analytical and preparative applications have been presented.

Design, synthesis & biological evaluation of ferulic acid-based small molecule inhibitors against tumor-associated carbonic anhydrase IX

Carbonic anhydrase IX (CAIX) is an emerging drug target for hypoxia associated cancers. To identify potent and selective inhibitors of CAIX, a small library of ferulic acid (FA) derivatives bearing triazole moiety has been designed, synthesized and evaluated against different human CA isoforms (CAII, CAVA & CAIX). Though most of the compounds showed CAIX inhibition in the micromolar range, compound 7i selectively inhibits CAIX in the nanomolar range (IC50 = 24 nM). In silico analysis revealed binding of 7i with the catalytically important amino acid residues of CAIX. Further, cell-based studies indicate that 7i inhibits the activity of CAIX, decreases the epithelial to mesenchymal transitions, induces apoptosis, inhibits cell migration and colonization potential of cancer cells. Taken together, these results emphasized the use of 7i as a prospective pharmacological lead molecule in CAIX targeted anticancer therapeutics.

Synthesis and discovery of asiatic acid based 1,2,3-triazole derivatives as antitumor agents blocking NF-κB activation and cell migration

A series of asiatic acid (AA) based 1,2,3-triazole derivatives were designed, synthesized and subjected to a cell-based NF-κB inhibition screening assay. Among the tested compounds, compound 6k displayed impressive NF-κB inhibitory activity with an ICsub

Synthesis, characterization, and pharmacological studies of ferrocene-1H-1,2,3-triazole hybrids

A series of ferrocene-1H-1,2,3-triazole hybrids namely 1-(4-nitrophenyl)-4-ferrocenyl-1H-1,2,3-triazole (1), 1-(4,4′-dinitro-2-biphenyl)-4-ferrocenyl-1H-1,2,3-triazole (2), 1-(3-chloro-4-fluorophenyl)-4-ferrocenyl-1H-1,2,3-triazole (3), 1-(4-bromophenyl)-

Benzooxadiazaole-based D-A-D co-oligomers: Synthesis and electropolymerization

Four D-A-D type co-oligomers have been synthesized by Stille condensation between monostannyl derivatives of furan/thiophene/selenophene/3,4- ethylenedioxythiophene (EDOT) and 4,7-dibromo-benzo[1,2,5]oxadiazole. All these co-oligomers were successfully electrochemically polymerized in dichloromethane and characterized by spectroelectrochemistry. All four polymers possess narrow optical band gap. Spectroelectrochemical studies of polymer films on indium tin oxide revealed that the replacement of donor EDOT with furan/thiophene/ selenophene has affected the low-energy charge-carrier (bipolaron) formation significantly. Kinetic studies based on chronoamperometry show that the polymer P5 (EDOT-capped benzo[1,2,5]oxadiazole system) possess better electrochromic property with high transmittance (66%) in visible region than the other copolymers.

Synthesis, characterization and thermal behavior study of new 1,2,3-triazole derivatives containing 1,3,4-oxadiazole ring

In this present work, a series of new 1-(substituted-phenyl)-1H-1,2,3-triazolyl-4-carboxylic acid derivatives was synthesized via copper (I) catalyzed azide-alkyne cycloaddition reaction. Since these synthesized 1,2,3-triazole compounds containing a carbo

Cellulose sulphuric acid as a biodegradable catalyst for conversion of aryl amines into azides at room temperature under mild conditions

This article describes simple and efficient method for the diazotization and azidation of different aromatic amines over cellulose sulphuric acid, sodium nitrite and sodium azide under mild conditions at room temperature. Various aryl amines possessing electron-withdrawing groups or electron-donating groups have been converted into the corresponding aryl azides with 71-99% yields. The use of mild reaction conditions, avoids the use of harmful acids and toxic solvents and short reaction times are advantages of this methodology. The selected catalyst is found to be highly efficient and recyclable.