74-39-5Relevant articles and documents
Azo-dyes based small bifunctional molecules for metal chelation and controlling amyloid formation
Rana, Monika,Cho, Hong-Jun,Roy, Tapta Kanchan,Mirica, Liviu M.,Sharma, Anuj K.
, p. 419 - 429 (2018)
Chemical tools are needed to discover new effective drugs for tackling multifaceted complex neurodegenerative diseases like Alzheimer's disease (AD). Multifunctional nature of two compounds, 5-((4-nitrophenyl)diazenyl)quinolin-8-ol (HL1) and 4-((4-nitrophenyl)diazenyl)benzene-1,3-diol (HL2) is reported w.r.t. their ability to bind Cu2+ ions and amyloid aggregates related to AD. HL1 and HL2 have half congo-red type azo-stilbene structural framework incorporated with metal chelating groups, designed to chelate metal ions from metal-amyloid species. Metal binding studies of HL1 and HL2 are established by the methods of Job's Plot, UV-vis spectra with metal ions and stability constant determination. In addition, their metal complexes are isolated, purity checked by elemental analysis, spectroscopically characterized and their structural analyses were obtained from DFT based calculations including binding energy determination. Chicken egg white Lysozyme (CEWL) was used as a model peptide for fibrillation studies. HL1 is found as an excellent colorimetric sensor for amyloid fibrils. Inhibitory effect of HL1 and HL2 and their isolated metal complexes L1-Cu and L2-Cu on CEWL fibrillation was studied using ThT and ANS fluorescence assay along with TEM imaging. In addition, the cell toxicity studies on these compounds suggest that although azo dyes may be non-toxic but having a nitro-substitution lead to significant cell toxicity. Overall, these results suggest that this new class of multifunctional small molecules can interact with amyloids as well as metal ions and could be potential anti-aggregation metal chelating agents.
Synthesis of nitroso-based bis-azo dyes and their dyeing properties for polyethylene terephthalate and polyamide
Augustine, Asiagwu K.,Otutu, Johnson O.
, p. 3949 - 3959 (2020/11/18)
The aim of this work is the synthesis of new azo nitroso-based dispersed dyes with better dyeing properties on synthetic fibers. In this regard, bis-azo nitroso naphthalene dyes were synthesized via the diazo coupling reactions of 4-nitroaniline with 1-hydroxy-2-nitrosonapthalene. Products formed were characterized by 1H and 13C NMR. Absorption values in the UV-vis spectra of the derivatives under study were quite close and they exhibited multiple maxima in the 386 - 513nm range. The dyeing process, dye exhaustion on polyethylene terephthalate (PET) and polyamide 6 (nylon 6) fabrics, and the durability of the dyes on the textile substrates were evaluated. It was found that the light fastness ratings of the dyed fabrics could reach grade 6/7 to 7, while washing fastness gave excellent values of grade 5 rubbing and perspiration fastness grades were rated at 4/5 to 5 on the International Geometric Scale. The results obtained suggested that the dyes could be used as disperse dyes on synthetic polymers fibres.
New generation of nitrite functionalized star-like polyvinyl imidazolium compound: Application as a nitrosonium source and three dimensional nanocatalyst for the synthesis of azo dyes
Shomali, Ashkan,Valizadeh, Hassan,Noorshargh, Saeideh
, p. 409 - 418 (2017/07/24)
The compounds with three-dimensional and ionic structures have attracted considerable attentions because of their unique characteristics as a drug carrier and catalyst. Star-like poly ionic compounds are a new generation of three-dimensional structures which have both; the exclusive ionic features and three-dimensional structures. Recently, we reported the synthesis of diazonium salts from aniline derivatives using carboxyl and nitrite functionalized graphene quantum dots. Methods: Nitrite-functionalized star-like polyionic (NFSP) compound was synthesized as a new generation of three-dimensional nanocatalyst. Herein, the use of NFSP as an efficient reagent and nanocatalyst for the diazotization of aniline derivatives and subsequent synthesis of azo dyes via the reaction with active phenolates under solvent-free conditions was reported. Results: In order to demonstrate the positive impact of NFSP efficiency, the reaction times and yields of the products were compared with other methods and catalysts which have been reported previously. The brilliant performance of NFSP can be ascribed to multifunctional reagent and also trapping the ingredient within catalyst cavities. Conclusion: A highly effective and cost-effective method has been developed for the preparation of azo dyes. In reported method, new three-dimensional catalyst with highly ionic characteristic and multifunctional nitrosonium source is available. These special features reduced the required amount of catalyst, reaction time and also increased the efficiency of catalyst.
Convenient and rapid diazotization and diazo coupling reaction via aryl diazonium nanomagnetic sulfate under solvent-free conditions at room temperature
Koukabi, Nadiya,Otokesh, Somayeh,Kolvari, Eskandar,Amoozadeh, Ali
, p. 12 - 17 (2015/10/05)
For the first time, nanomagnetic-supported sulfonic acid is used for conversion of several types of aromatic amine, containing electron-withdrawing groups as well as electron-donating groups to the corresponding azo dyes in excellent yield. The synthesis of these compounds is described by the sequential diazotization-diazo coupling of various aromatic amines with sodium nitrite, nanomagnetic supported sulfonic acid and coupling agents under solvent-free conditions at room temperature. This new method offers several advantages including short reaction time, mild reaction conditions, avoidance of harmful acids, and simple work-up procedure. More importantly, aryldiazonium salts supported on magnetic nanoparticles (aryl diazonium nanomagnetic sulfate) were sufficiently stable to be kept at room temperature in the dry state.
Synthesis of a nitrite functionalized star-like poly ionic compound as a highly efficient nitrosonium source and catalyst for the diazotization of anilines and subsequent facile synthesis of azo dyes under solvent-free conditions
Valizadeh, Hassan,Shomali, Ashkan,Ghorbani, Jalal,Noorshargh, Saeideh
, p. 64 - 71 (2015/03/04)
Nitrite functionalized star-like poly ionic (NFSPI) compound was synthesized and used as a highly efficient nitrosonium source and catalyst for the conversion of aniline derivatives to diazonium salts. Azo dyes were prepared via in situ azo-coupling reaction of these diazoniums with active aromatic compounds under solvent-free conditions in very short reaction time in excellent yields. NFSPI plays dual role as a three-dimensional nitrosonium source and catalyst because of its poly ionic characteristic. The isolated products were confirmed with FT-IR spectrum, 1H-NMR, 13C-NMR spectroscopy and CHNSO analysis. The structure of heterogeneous reagent and catalyst was confirmed by FT-IR spectrum, SEM images, EDX and CHNSO analysis. Yields and reaction times for the synthesis of a variety of products via this procedure were compared with reported values in literature.
Carboxyl and nitrite functionalized graphene quantum dots as a highly active reagent and catalyst for rapid diazotization reaction and synthesis of azo-dyes under solvent-free conditions
Valizadeh, Hassan,Shomali, Ashkan,Nourshargh, Saideh,Mohammad-Rezaei, Rahim
, p. 522 - 528 (2015/03/18)
Carboxyl and nitrite functionalized graphene quantum dots was prepared from carboxyl and hydroxyl functionalized graphene quantum dots using NaNO2 in the absence of mineral acids. This functional group conversion was confirmed by FT-IR spectroscopy, photoluminescence and X-ray diffraction. The carboxyl and nitrite functionalized graphene quantum dots was used as an effective nitrosonium ion source and reusable catalyst for the efficient diazotization of a variety of arylamines without using any additional acid. Subsequent azo-coupling of these freshly prepared diazonium salts with a range of active aromatic compounds led to the requisite azo-dyes in excellent yields in very short reaction times with a simple experimental procedure.
A new nitrite ionic liquid (IL-ONO) as a nitrosonium source for the efficient diazotization of aniline derivatives and in-situ synthesis of azo dyes
Valizadeh, Hassan,Shomali, Ashkan
experimental part, p. 1138 - 1143 (2012/03/27)
A new task-specific nitrite containing ionic liquid derived from the O-nitrosation of N-methyl-N-hydroxybutylimidazolinium chloride was synthesized and used as a source of nitrosonium ion to affect the efficient diazotization of arylamines. The diazonium salts thus obtained were coupled, using standard experimental procedures, to a range of tertiary anilines, phenols and naphthols to afford the requisite azo dyes in good yield. The diazotization and subsequent azo-coupling generated the related azo dyes at 0-5 °C in short reaction times with a simple experimental procedure.
Nanoparticles of organosilane-based nitrite ionic liquid immobilized on silica for the diazotization of aniline derivatives and subsequent synthesis of azo dyes
Valizadeh, Hassan,Amiri, Mohammad,Hosseinzadeh, Fatemeh
experimental part, p. 1308 - 1313 (2012/03/27)
Imidazolium based nitrite ionic liquid containing trimethoxysilyl group was prepared from the reaction of N-methylimidazole and (3-chloropropyl) trimethoxysilane. This ionic liquid was immobilized on silica covalently to give nanoparticles with the imidazolium nitrite moiety remaining intact. The diazotization reaction was performed as a model reaction to examine the activity of these nanoparticles as a nitrosonium source. Excellent performance was exhibited in the diazotization reaction of various aniline derivatives in the presence of HCl under mild heterogeneous conditions (room temperature and short reaction time). In-situ coupling of diazonium salts to a range of tertiary anilines, phenols and naphthols afforded the requisite azo dyes in good yield, using standard experimental procedures.
Ionic liquid 1-(3-trimethoxysilylpropyl)-3-methylimidazolium nitrite as a new reagent for the efficient diazotization of aniline derivatives and in situ synthesis of azo dyes
Valizadeh,Amiri,Shomali,Hosseinzadeh
experimental part, p. 495 - 501 (2012/07/13)
A new ionic liquid 1-(3-trimethoxysilylpropyl)-3-methylimidazolium nitrite was synthesized. This ionic liquid was used as a convenient nitrosonium source in diazotization of arylamines into their corresponding diazonium salts which were converted into their related azo dyes via the in situ azo-coupling with aniline derivatives or phenolic compounds. The diazotization of anilines in this ionic liquid and subsequent azo-coupling generated the related azo dyes in good to excellent yields at 0-5 °C in short reaction times via a simple experimental procedure.
Can be azo dyes obtained by grinding under solvent-free conditions?
Noroozi-Pesyan, Nader,Khalafy, Jabbar,Malekpoor, Zahra
experimental part, p. 1018 - 1027 (2010/09/10)
The solid-solid reactions of some electron-donors with sulfanilic acid in the presence of solid sodium nitrite afford azo dyes by self-catalyzed diazotization of sulfanilic acid (2) under solvent-free conditions with moderate yields. Also the reactions of some electron-donors with diazotization of o-nitroaniline (5), m-nitroaniline (6) and p-nitroaniline (7) in the presence of solid sodium nitrite catalyzed by p-toluenesulfonic acid (PTSA) afford azo dyes under solvent-free conditions in good yields. This new method totally avoids the use of acids, alkalies, and toxic and/or expensive solvents in diazotization and diazo coupling reactions.
