121-73-3Relevant articles and documents
Superactive iodination reagent on a base of iodine chloride and silver sulfate
Chaikovski, Vitold K.,Kharlova, Tatjana S.,Filimonov, Victor D.,Saryucheva, Tamara A.
, p. 748 - 750 (1999)
After reaction of ICl and Ag2SO4 in sulfuric acid and separation of resulting AgCl a stable solution is formed, containing very active forms of electrophilic iodine. This solution has a powerful iodination ability with respect to aromatic compounds. Deactivated arenes are iodinated easily and in mild conditions by action of this new reagent in generally good yields of the iodoarenes.
Acid-Catalyzed Nucleophilic Aromatic Photosubstitution. A Reconsideration of Protonation in Excited States of Nitrobenzenes
Wubbels, Gene G.,Susens, Douglas P.,Cuoghlin, E. Bryan
, p. 2538 - 2542 (1988)
3-Bromonitrobenzene is photosubstituted inefficiently but cleanly by chloride ion to give 3-chloronitrobenzene.The photosubstitution is catalyzed by hydronium ion; the limiting quantum yield of 0.021 at infinite +> and 3.0 M -> is only 2-fold higher than the quantum yield (0.011) of the uncatalyzed photosubstitution at 3.0 M ->.The limiting quantum yield at infinite chloride ion concentration with no added acid is also 0.021.That 2-propanol does not intervene on the photosubstitution pathway to cause photoreduction indicates that radical intermediates are not involved, and the absence of deuterium incorporation on the aromatic ring accompanying photosubstitution indicates that the catalysis does not involve formation of a dihydrobenzene intermediate.The reaction appears to be an example of the so-called mechanism and the catalysis to be a manifestation of protonation of the 3?,?* state, which is the higher energy triplet state in 3-bromonitrobenzene.
Green route for the chlorination of nitrobenzene
Boltz, Marilyne,De Mattos, Márcio C.S.,Esteves, Pierre M.,Pale, Patrick,Louis, Benoit
, p. 1 - 8 (2012)
A new green chlorination process of deactivated aromatics has been developed, being environmental-friendly and allowing the continuous chlorination of 1.7 kg nitrobenzene/kg catalyst per day. The triple novelty consists of using a non-conventional chlorination agent, the trichloroisocyanuric acid (TCCA, C3N3O3Cl3), along with solid acid catalysts (mainly zeolites) in a continuous flow reactor system. Different zeolites and solid acids have been tested in the chlorination of nitrobenzene, chosen as a model deactivated aromatic substrate. HUSY zeolite was found as the more promising catalyst for performing the chlorination of nitrobenzene, with good conversions (39-64%) at high selectivity toward monochlorinated products (90-99%). Finally, it is worthy to note that HUSY zeolite could be reused for at least five successive runs.
Preparation method of M-nitrochlorobenzene
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Paragraph 0014-0022, (2021/07/08)
The invention discloses a preparation method of m-nitrochlorobenzene. The method comprises the step of preparing m-nitrochlorobenzene by taking chlorobenzene as a raw material and N-nitropyrazole and H2SO4 as nitrating agents. The method specifically comprises the following steps: adding 8ml of 98% sulfuric acid into a four-neck bottle, dropwise adding 0.012 mol of chlorobenzene into concentrated sulfuric acid under the conditions that the mechanical stirring speed is 300 to 400r/min and the temperature is 20 DEG C, heating in a water bath to 60 DEG C after the charging is completed, averagely dividing 0.024 mol of N-nitropyrazole into four parts, sequentially adding the four parts of N-nitropyrazole at the temperature, heating the reaction system in the charging process, adding materials again after the temperature is reduced to the initial temperature, keeping stirring after the materials are added, reacting at the constant temperature of 65 DEG C for 6 hours, pouring reaction liquid into a container filled with ice blocks while the reaction liquid is hot, and stirring to reduce the temperature of the solution to 5 DEG C to separate out light yellow substances.
Low-temperature and highly efficient liquid-phase catalytic nitration of chlorobenzene with NO2: Remarkably improving the para-selectivity in O2-Ac2O-Hβ composite system
Deng, Renjie,Liu, Pingle,Luo, He'an,Ni, Wenjin,You, Kuiyi,Zhao, Fangfang
, (2020/02/26)
In this work, we developed a low-temperature and efficient approach for the highly selective preparation of valuable p-nitrochlorobenzene from the liquid-phase catalytic nitration of chlorobenzene with NO2 in O2-Ac2O-Hβ composite system. The results demonstrated that the introduction of molecular oxygen remarkably enhanced the chlorobenzene conversion and the cooperation catalysis of Hβ zeolite and Ac2O envidently improved the selectivity to para-nitro product. Under the optimized reaction conditions, 93.6 % of the selectivity to p-nitrochlorobenzene with 84.0 % of chlorobenzene conversion was obtained, and the ratio of p-nitrochlorobenzene to o-nitrochlorobenzene could reach up to 20.3. Furthermore, the selectivity distribution of nitration products was reasonably explained by the density functional theory (DFT) calculation. Finally, the possible nitration reaction pathway of chlorobenzene with NO2 was suggested in O2-Ac2O-Hβ composite catalytic system. The present work affords a new and mild nitration approach for highly selective preparation of valuable para-nitro products, and has potential industrial application prospects.
Synthesis of thioethers, arenes and arylated benzoxazoles by transformation of the C(aryl)-C bond of aryl alcohols
Chen, Bingfeng,Han, Buxing,Liu, Mingyang,Meng, Qinglei,Song, Jinliang,Zhang, Pei,Zhang, Zhanrong
, p. 7634 - 7640 (2020/08/14)
Transformation of aryl alcohols into high-value functionalized aromatic compounds by selective cleavage and functionalization of the C(aryl)-C(OH) bond is of crucial importance, but very challenging by far. Herein, for the first time, we report a novel and versatile strategy for activation and functionalization of C(aryl)-C(OH) bonds by the cooperation of oxygenation and decarboxylative functionalization. A diverse range of aryl alcohol substrates were employed as arylation reagents via the cleavage of C(aryl)-C(OH) bonds and effectively converted into corresponding thioether, arene, and arylated benzoxazole products in excellent yields, in a Cu based catalytic system using O2 as the oxidant. This study offers a new way for aryl alcohol conversion and potentially offers a new opportunity to produce high-value functionalized aromatics from renewable feedstocks such as lignin which features abundant C(aryl)-C(OH) bonds in its linkages.
A convenient room temperature ipso-nitration of arylboronic acid catalysed by molecular iodine using zirconium oxynitrate as nitrating species: An experimental and theoretical investigation
Mahanta, Abhijit,Gour, Nanda Kishor,Sarma, Plaban Jyoti,Borah, Raju Kumar,Raul, Prasanta Kumar,Deka, Ramesh Chandra,Thakur, Ashim Jyoti,Bora, Utpal
, (2019/05/15)
A simple and convenient protocol has been developed for ipso-nitration of arylboronic acid catalysed by molecular iodine at room temperature, using zirconium oxynitrate as the nitrating species. The protocol is applicable to electronically diverse aryl- and heteroarylboronic acid moieties under mild reaction conditions with good to excellent isolated yields. Furthermore, a theoretical investigation has been performed for the same reaction, and reaction profiles are modelled using modern density functional theory (DFT). DFT-based results support the experimentally observed results.
Method for preparing nitro compound by using graphene to catalyze carbon dioxide
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Paragraph 0033-0034, (2018/06/16)
The invention discloses a method for preparing a nitro compound by using graphene to catalyze carbon dioxide. A graphene material is applied to catalysis of a reaction of carbon dioxide and a nitrification substrate such as an aromatic compound to prepare the nitro compound. The method is used for replacing a traditional nitric acid/sulfur acid method to prepare the nitro compound, so that the atom utilization rate of the reaction is increased, the energy is saved, and the emission is reduced; and the method has the characteristic of atom economy during industrial preparation of the nitro compound.
Method for preparing nitro compound by using graphene to catalyze nitric oxide
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Paragraph 0037; 0038, (2018/06/16)
The invention discloses a method for preparing a nitro compound by using graphene to catalyze nitric oxide. A graphene oxide carbon material is used for catalysis of a reaction of nitric oxide and a nitrification substrate such as an aromatic compound to prepare the nitro compound. The method is used for replacing a traditional nitric acid/sulfur acid method to prepare the nitro compound, so thatthe atom utilization rate of the reaction is increased, the energy is saved, and the emission is reduced; and the method has the characteristic of atom economy during industrial preparation of the nitro compound.
Dimethyl sulfoxide-accelerated reductive deamination of aromatic amines with t-BuONO in tetrahydrofuran
Fang, Lu,Qi, Liang,Ye, Longfei,Pan, Zhentao,Luo, Wenjun,Ling, Fei,Zhong, Weihui
, p. 579 - 583 (2018/11/27)
An efficient method for the conversion of aryl amines into arenes by a one-pot reductive deamination has been achieved. It was found the reductive deamination using t-BuONO in tetrahydrofuran could be accelerated by dimethyl sulfoxide and provided the deamination products with good yields under mild conditions. A plausible mechanism is discussed.
