7150-24-5Relevant academic research and scientific papers
One-pot synthesis of azo compounds in the absence of acidic or alkaline additives
Cheng, Xin-Wang,Duan, Pan,Liu, Ting-Ting,Yan, Jiao-Zhao,Zeng, Yao-Fu
, p. 486 - 490 (2020/10/22)
A one-pot method for the synthesis of azo compounds by the reaction of β-naphthol with aryl amines using t-BuONO as the nitrosonium source in DCM at room temperature was developed. This method features mild reaction conditions, a simple experimental procedure, and is free of acidic or alkaline additives.
Mesomorphism dependence on terminal polar group in the nonlinear novel azoester series
Kher, Seema N.,Prajapati,Chandra, Raviprakash S.,Makwana
, p. 1 - 9 (2019/02/24)
Synthesis of a novel azoester homologous series is carried out with a view to understand and establish the effect of molecular structure on liquid crystal (LC) behaviors of a substance. Novel series consists of ten LC substances. All the homologs are enantiotropically nematogenic without exhibition of smectic property. Transition and melting temperatures, textures of LC are determined by an optical polarizing microscopy equipped with a heating stage. Textures of nematic phase are threaded or schlieren. Transition curves of a phase diagram behaved in normal manner. Nematic–isotropic transition curve exhibited odd–even effect. Analytical and spectral data supported and confirmed the structures of homologues.
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.
An environmentally friendly approach to the green synthesis of azo dyes in the presence of magnetic solid acid catalysts
Safari, Javad,Zarnegar, Zohre
, p. 17738 - 17745 (2015/06/15)
A solvent-free, efficient and green approach for the synthesis of azo dyes has been developed by the diazo coupling reactions of aromatic amines with β-naphthol in the presence of sulfonic acid functionalized magnetic Fe3O4 nanoparticles (Fe3O4@SiO2-SO3H) by a grinding method at room temperature. This green methodology aims to overcome the limitations and drawbacks of the previously reported methods such as low temperature, use of acids, alkalis and toxic solvents, instability of diazonium salts at room temperature, modest yields, and long reaction times. Moreover, the attractive advantages of the process include mild conditions with excellent conversions, simple product isolation process, inexpensive procedure and recyclability of the magnetic catalyst. This journal is
New dry arenediazonium salts, stabilized to an exceptionally high degree by the anion of o-benzenedisulfonimide
Barbero, Margherita,Crisma, Marco,Degani, Lacopo,Fochi, Rita,Perracino, Paolo
, p. 1171 - 1175 (2007/10/03)
Arenediazonium o-benzenedisulfonimides 3 (20 examples, yield >90%) were prepared in the dry state by diazotization of aromatic amines with (-pentyl nitrite and o-benzenedisulfonimide in glacial acetic acid or formic acid at 0-5°C. Unlike most diazonium salts in the dry state, salts 3 are very highly stable.
para-Bromination of Anilinium Ions in the Presence of Nitrosonium Hydrogen Sulfate in Concentrated Sulfuric Acid
Gorelik, M. V.,Lomzakova, V. I.,Khamidova, E. A.,Shteiman, V. Ya.,Kuznetsova, M. G.,Andrievskii, A. M.
, p. 508 - 512 (2007/10/03)
Aniline and its o-, m-, and N-substituted derivatives are converted to corresponding 4-bromo derivatives in concentrated sulfuric acid under the action of bromine and nitrosonium hydrogen sulfate; in the absence of the latter, no bromination occurs.
Kinetics and Mechanism of the Diazo Coupling Reaction of Arenediazo Methyl Ethers with β-Naphthol. Part 1. The Rates of Reaction in Nonaqueous Acid Solutions
Masoud, Nabil K.,Ishak, Mona F.
, p. 927 - 932 (2007/10/02)
Rate data are presented for the diazo coupling reaction of arenediazo methyl ethers with β-naphthol in solutions of dioxane, ethanol, and propan-2-ol acidified with hydrochloric acid at 25 deg C.Over range of HCl concentrations studied, pseudo-first-order rate constants were obtained and the reaction was found to be of first order in diazo ether.The relationship between the observed rate constants (kobs.) and hydrochloric acid concentration (cHCl) was found to be non-linear.Correlations of reaction rates with the Hammett acidity function (H0) and with the Hammett substituent constant (?x) conform with a mechanism in which the slow step is unimolecular decomposition of the protonated diazo ether, DEH(1+), to the coupling entity, the diazonium ion, D(1+), which instantly reacts with β-naphthol to give the azo dye.
3-Aryl-1-tetrazol-5-yltriazenes, Bench-stable Arenediazonium Ion Synthons: Synthesis of Biaryls and Aryl Halides
Butler, Richard N.,O'Shea, Paul D.,Shelly, Declan P.
, p. 1039 - 1042 (2007/10/02)
3-Aryl-1-tetrazol-5-yltriazenes have been used as a bench-stable source of diazonium ions for the synthesis of substituted biaryls, aryl halides (iodides, bromides, and chlorides) and azo dyes.The dediazoniation process when induced by trihalogenoacetic acid or acetic acid did not involve free radicals.
A Simple Route for the Synthesis of Chlorosubstituted Arylazobenzenes, Arylazonaphtalenes, and Arylazopyrazoles
Guenther, R.,Jaehne, E.,Hartmann, H.,Schulze, M.
, p. 945 - 954 (2007/10/02)
The reaction of arylazophenoles and arylazohydroxypyrazoles (or their tautomer hydrazones) 10, 11, and 15 with POCl3 in dimethylformamide yields chlorosubstituted arylazobenzenes or arylazopyrazoles 12, 13 and 16, resp., in moderate to high yields.The substitution of the OH-group by the Cl-moiety is favoured by acceptor substituents in the aryl fragments ortho- and/or para-linked to the azo group.In case that arylazocompounds derived from resorcinol are used the substitution reaction runs in a stepwise manner giving raise to the formation of o-hydroxy-p-chlorosubstit uted azo compounds 18 primarily and then of dichlorosubstituted azo compounds 19.
