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1516-58-1

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1516-58-1 Usage

General Description

2-nitrophenyl azide is a chemical compound with the molecular formula C6H4N4O2. It is a yellow to orange crystalline powder and is commonly used as a photolabile crosslinker in bioconjugation and affinity labeling studies. 2-nitrophenyl azide is often utilized in photoaffinity labeling experiments to study protein-protein interactions and receptor-ligand interactions. When exposed to ultraviolet light, it undergoes a photochemical reaction to form a highly reactive nitrene, which can then covalently bind to nearby biomolecules. Additionally, it has been used in the development of photoactive surfaces for the immobilization of biomolecules and in the synthesis of photoreactive polymers for use in drug delivery systems and biomaterials. However, it is important to note that 2-nitrophenyl azide is a hazardous and potentially explosive compound, and appropriate safety precautions should be taken when handling and working with this chemical.

Check Digit Verification of cas no

The CAS Registry Mumber 1516-58-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,1 and 6 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1516-58:
(6*1)+(5*5)+(4*1)+(3*6)+(2*5)+(1*8)=71
71 % 10 = 1
So 1516-58-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H5N4O2/c7-9-8-5-3-1-2-4-6(5)10(11)12/h1-4,7H/q+1

1516-58-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name o-Nitrophenyl azide

1.2 Other means of identification

Product number -
Other names ortho-azidonitrobenzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1516-58-1 SDS

1516-58-1Relevant articles and documents

Preparation of aryl azides from aromatic amines in N-methyl-2-pyrrolidonium bisulfate

Hajipour, Abdol Reza,Mohammadsaleh, Fatemeh

, p. 451 - 455 (2011)

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

Cardillo, Paolo,Gigante, Lucia,Lunghi, Angelo,Zanirato, Paolo

, p. 191 - 198 (2010)

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).

Synthesis and antimicrobial potential of nitrofuran-triazole congeners

Kamal, Ahmed,Hussaini, S. M. Ali,Sucharitha, M. Lakshmi,Poornachandra,Sultana, Faria,Ganesh Kumar

, p. 9388 - 9397 (2015)

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

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

Abid, Mohammad,Alajmi, Mohamed F.,Aneja, Babita,Daniliuc, Constantin G.,Hasan, Phool,Hassan, Md. Imtaiyaz,Hussain, Afzal,Khan, Parvez,Mohsin, Mohd.,Queen, Aarfa,Rizvi, M. Moshahid A.,Shamsi, Farheen

, (2020)

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

Haque, Ashanul,Hsieh, Ming-Fa,Hassan, Syed Imran,Haque Faizi, Md. Serajul,Saha, Anannya,Dege, Necmi,Rather, Jahangir Ahmad,Khan, Muhammad S.

, p. 536 - 545 (2017)

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)-

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

Nahi, Riyadh J.,Kuwait, Zainab I.

, p. 416 - 422 (2019)

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

1,2,3-Triazole-quinazolin-4(3H)-one conjugates: evolution of ergosterol inhibitor as anticandidal agent

Masood, Mir Mohammad,Irfan, Mohammad,Khan, Parvez,Alajmi, Mohamed F.,Hussain, Afzal,Garrison, Jered,Rehman, Md. Tabish,Abid, Mohammad

, p. 39611 - 39625 (2018)

The present study describes the synthesis of 1,2,3-triazole-quinazolinone conjugates (5a-q) from ethyl 4-oxo-3-(prop-2-ynyl)-3,4-dihydroquinazoline-2-carboxylate and phenyl azide/substituted phenyl azides employing Cu(i) catalysed Huisgen 1,3-dipolar cycloaddition. The corresponding acids (6a-q) were obtained by hydrolysis of esters (5a-q) to study the effect of these functionalities on the biological activity. All synthesized compounds were screened for in vitro anticandidal evaluation against Candia albicans, Candida glabrata and Candida tropicalis strains. The results indicated that compound 5n showed potent anticandidal activity with IC50 in the range of 8.4 to 14.6 μg mL?1. Hemolytic activity using human red blood cells (hRBCs) and cytotoxicity by MTT assay on human embryonic kidney (HEK-293) cells revealed the non-toxic nature of the selected compounds. Growth kinetic study with compound 5n showed its fungicidal nature as no significant growth of Candida cells was observed even after 24 h. Cellular ergosterol content was determined in the presence of different concentrations of 5n to measure the activity of lanosterol 14α-demethylase indirectly. The results showed significant disruption of the ergosterol biosynthetic pathway through inhibition of lanosterol 14α-demethylase activity supported by docking studies (PDB: 5v5z). Overall, this study demonstrates the anticandidal potential of 5n which can serve as the lead for further structural optimization and SAR studies.

Ionic liquids/[bmim][N3] mixtures: Promising media for the synthesis of aryl azides by SNAr

D'Anna, Francesca,Marullo, Salvatore,Noto, Renato

, p. 6224 - 6228 (2008)

(Formula Presented) The nucleophilic aromatic substitution of some activated aryl or heteroaryl halides has been performed in ionic liquid solution, using the 1-butyl-3-methylimidazolium azide as a nucleophile. The reaction course was studied varying the

A library of 1,2,3-triazole-substituted oleanolic acid derivatives as anticancer agents: Design, synthesis, and biological evaluation

Wei, Gaofei,Luan, Weijing,Wang, Shuai,Cui, Shanshan,Li, Fengran,Liu, Yongxiang,Liu, Yang,Cheng, Maosheng

, p. 1507 - 1514 (2015)

A series of novel oleanolic acid coupled 1,2,3-triazole derivatives have been designed and synthesized by employing a Cu(i) catalyzed Huisgen 1,3-dipolar cycloaddition reaction. The anti-proliferative evaluation indicated that some compounds exhibited exc

Design, Synthesis and Evaluation of a Series of 1,5-Diaryl-1,2,3-triazole-4-carbohydrazones as Inhibitors of the YAP-TAZ/TEAD Complex

Gibault, Floriane,Sturbaut, Manon,Coevoet, Mathilde,Pugnière, Martine,Burtscher, Ashley,Allemand, Frédéric,Melnyk, Patricia,Hong, Wanjin,Rubin, Brian P.,Pobbati, Ajaybabu V.,Guichou, Jean-Fran?ois,Cotelle, Philippe,Bailly, Fabrice

, p. 2823 - 2844 (2021/07/10)

Starting from our previously reported hit, a series of 1,5-diaryl-1,2,3-triazole-4-carbohydrazones were synthesized and evaluated as inhibitors of the YAP/TAZ-TEAD complex. Their binding to hTEAD2 was confirmed by nanodifferential scanning fluorimetry, an

Synthesis and Molecular Docking of novel 1,3-Thiazole Derived 1,2,3-Triazoles and In vivo Biological Evaluation for their Anti anxiety and Anti inflammatory Activity

Ankali, Kariyappa N,Rangaswamy, Javarappa,Shalavadi, Mallappa,Naik, Nagaraja,Krishnamurthy, Ganga naik

, (2021/04/09)

Heterocyclic rings such as thiazole and triazole are considered as privileged moieties, since they constitute several drugs for biological treatment. In this work, a novel series of 1, 3-thiazole linked 1,2,3-triazole derivatives were designed and synthesized according to convenient synthetic procedures. All the synthesized compounds are characterized by 1H NMR, 13C NMR and LCMS techniques. The molecular docking was studied to illustrate the binding interactions of target molecules with GABAA receptor. The synthesized compounds containing 1,3-thiazole and 1,2,3-triazole ring, the presence of these rings in each molecule may lead to have potential in vivo anti-anxiety and anti-inflammatory properties. The in vivo activity result revealed that some of the compounds possessed statistical significant therapeutic efficacy. Anti-anxiety screening on mice indicated that all the target compounds (5mg/kg) exhibited certain extent of an anxiolytic effect by increasing time spent on open arms and the percentage of open arm entries as compared to controlled group. More importantly, among the newly synthesized compounds (6h) and (6i) have strong anti-anxiety against mice. The non steroidal anti-inflammatory activity drugs (NSAIDs) are plays a very important role to prevent the growth of cyclooxygenase enzymes which are responsible for inflammation and pain. The results show that the following compounds 6e, 6g, 6h, and 6k are having maximum anti inflammatory activity against carrageenan induced acute inflammation in rats comparable to diclofenac as reference drug. Molecular docking simulations were employed to find out the important binding modes responsible for the anti anxiety activity, thus supporting their effective anti-anxiety efficacy.

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