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573-56-8Relevant academic research and scientific papers
Method for synthesizing benzoxazole compound by using nitration by-products of aromatic hydrocarbon and application of benzoxazole compound
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Paragraph 0043-0045; 0059-0061, (2019/09/14)
The invention discloses a method for synthesizing a benzoxazole compound by using nitration by-products of aromatic hydrocarbon and application of the benzoxazole compound. The method comprises the main process: performing step-by-step crystallization on nitration products of a 2,4-dinitrochlorobenzene production enterprise so as to obtain 2,4-dinitrochlorobenzene, 2,6-dinitrochlorobenzene (I) anda small amount of residues, adopting the obtained 2,6-dinitrochlorobenzene (I) as the main starting material, and performing hydrolysis, selective catalytic hydrogenation reduction, cyclization, halogenation, carbon-carbon coupling and other processes so as to synthesize the benzoxazole compound, wherein the obtained compound can be used as a main raw material to synthesize a series of chemical intermediates with important application, and the chemical intermediates include o-aminophenol, 2-amino-4-nitrophenol, 2-amino-5-nitrophenol and hydrochloride of o-aminophenol, 2-amino-4-nitrophenol, 2-amino-5-nitrophenol. Through the method, the industrial by-products are converted into high value-added aromatic aminophenol products, industrial hazardous waste of the 2,4-dinitrochlorobenzene production enterprise is reduced, the scope of products of the enterprise is widened, and the economic benefits of enterprise are increased.
Magnetically recyclable Pd/Fe3O4/g-C3N4 as efficient catalyst for the reduction of nitrophenol and suzuki-miyaura reaction at room temperature
Yang, Yingwei,Tang, Ruiren
supporting information, p. 544 - 547 (2018/04/09)
Herein, we present the design and synthesis of a novel magnetic stable and recyclable catalyst Pd/Fe3O4/g-C3N4 with approachable active palladium nanoparticles (Pd NPs) based on the platelet-like graphitic carbon nitrides (g-C3N4). The Pd NPs, g-C3N4 and magnetic particles (Fe3O4) are tightly connected through non-covalent interactions owing to the layered structure of g-C3N4 with abundant nitrogen atoms, facilitating the stability of Pd/Fe3O4/g-C3N4 and activating the Pd NPs at the same time. The Pd/Fe3O4/g-C3N4 catalyst with a narrow particle size distribution (2.55 nm) of Pd NPs displayed the maintenance of the planar structure of g-C3N4. The activity parameter of the catalyst turned out to be excellent (12.4 s11￠mM11) by fitting the curves derived from the reduction of nitrophenol. Meanwhile, the Suzuki-Miyaura coupling reaction at room temperature processed smoothly with the Pd/Fe3O4/g-C3N4 catalyst. It is meaningful to stress that 2-bromobenzonitrile and p-tolylboronic acid could afford the medical intermediate sartanbiphenyl at total conversion without side reactions in 25 min. Furthermore, the nanocatalyst owes the properties of easy recycling using a powerful magnet as well as high turnover frequency (at least 5 runs) with retention of high catalytic activity.
Nitrogen Oxides and Nitric Acid Enable the Sustainable Hydroxylation and Nitrohydroxylation of Benzenes under Visible Light Irradiation
Hofmann, Laura Elena,Mach, Leonard,Heinrich, Markus R.
supporting information, p. 431 - 436 (2017/12/15)
A new type of waste recycling strategy is described in which nitrogen oxides or nitric acid are directly employed in photocatalyzed hydroxylations and nitrohydroxylations of benzenes. Through these transformations, otherwise costly denitrification can be combined with the synthesis of valuable compounds for various applications.
Microwave assisted synthesis of nitro phenols from the reaction of phenols with urea nitrate under acid-free conditions
Verma, Sanny,Pandita, Sangeeta,Jain, Suman L.
, p. 1320 - 1322 (2014/03/21)
Urea nitrate was found to be an inexpensive, acid-free, and safe nitrating agent that provides mononitration of phenols and substituted phenols in excellent yields with exclusive ortho-selectivity under microwave irradiation. Microwave assisted reactions reduced the reaction times substantially and enhanced the product yields from good to excellent within shorter reaction times.
A facile demethylation of ortho substituted aryl methyl ethers promoted by AlCl3
Du, Zhen-Ting,Lu, Jing,Yu, Hong-Rui,Xu, Yan,Li, An-Pai
experimental part, p. 222 - 227 (2010/08/04)
An efficient and practical demethylation of ortho substituted aryl methyl ethers using AlCl3 has been developed. This method gives a high conversion, is simple to operate and is cost-effective. A mechanism involving the complexation of AlCl3 with the OMe and the adjacent electron withdrawing group is proposed. Many functional groups can be tolerated in the demethylation process, and 29 examples gave a demethylated product in a yield of 90-98%.
Reactivity of α-amino acids in the N-acylation with benzoic acid esters in aqueous dioxane
Ishkulova,Oparina,Kochetova,Kustova,Kalinina,Kuritsin
experimental part, p. 964 - 967 (2011/01/07)
The effect of the nitro group as a substituent in the phenoxide part of phenyl benzoate on the rate of N-acylation of glycine, L-proline,and L-valine in the water (40 wt %)-dioxane solvent was studied. The activation parameters of glycine reactions with the esters were measured. The existence of compensation effect and the linear relation of the logarithms of the acylation constants to the Hammett constants were revealed. The energy of the LUMO of esters can serve as the descriptors of the easters reactivity. Pleiades Publishing, Ltd., 2010.
From N-(dinitrophenyl) amino acids to benzimidazole N-oxides. Synthesis, kinetics and mechanism
Bujan, Elba I.,Salum, Maria Laura
, p. 187 - 195 (2007/10/03)
Several benzimidazole N-oxide derivatives were synthesized in very good yields by heating under reflux the corresponding N-(2,4- or 2,6-dinitrophenyl) amino acid derivative with NaOH in 60% 1,4-dioxane-H2O. The N-oxides obtained from glycine and α- and β-alanine derivatives lost the carboxylic group. The observed rate constant for the reaction of N-(2,4-dinitrophenyl) glycine (2a) in 10% 1,4-dioxane-H2O to give 5-nitro-1H-benzimidazole-3-oxide (4a) is first order on [NaOH]; the second-order rate constant is kN=1.7 × 10-3 M-1 S-1. The mechanism proposed includes the formation of an N-alkylidene 2-nitrosoaniline-type intermediate as the rate-determining step. Copyright
Nitrophenol derivatives oxidized by cerium(IV) ammonium nitrate (CAN) and their cytotoxicity
Pan, Wen-Bin,Wei, Li-Mei,Wei, Li-Lan,Wu, Chin-Chung,Chang, Fang-Rong,Wu, Yang-Chang
, p. 581 - 588 (2007/10/03)
Oxidation of a series of phenols with cerium(IV) ammonium nitrate (CAN) in acetonitrile undermild conditions yields the mixture of corresponding nitrophenols. In the cases of methylphenols and hydroxy-carboxylic acids, the steric effect may reduce the nitration reaction. Compounds 3 a and 4b showed selective activities to Hep 3B and Hep G2 cancer cell lines, respectively. Compound 2c showed selective activities to Hep G2 and MDA-MB-231 cancer cell lines. Further more, com pound 10b showed selective activities to Hep G2, Hep 3B, MCF-7 and MDA-MB-231 cancer cell lines.
Leaving group effects on the mechanism of aromatic nucleophilic substitution (SnAr) reactions of some phenyl 2,4,6-trinitrophenyl ethers with aniline in acetonitrile
Crampton, Michael R.,Emokpae, Thomas A.,Howard, Judith A.K.,Isanbor, Chukwuemeka,Mondal, Raju
, p. 65 - 70 (2007/10/03)
Kinetic studies are reported for the reactions with aniline in acetonitrile of a series of X-phenyl 2,4,6trinitrophenyl ethers [X = H, 2-, 3-, 4-CH3,2,4-, 2,6-(CH3)2,2-, 3-, 4-NO 2,2,4-, 2,6-(NO2)2]. X-ray crystal structures for X = H, 2,6-(CH3)2 and 2,6-(NO2) 2 are reported and provide evidence for steric crowding around the 1-position of these molecules. Nevertheless, the kinetic data show that increasing substitution does not sterically inhibit nucleophilic attack by aniline and an 'early' transition state is likely. In general, the reactions are base catalysed; interpreted as rate-limiting deprotonation of the zwitterionic intermediates. Only with the dinitro derivatives is an uncatalysed reaction involving intramolecular proton transfer observed and when X = 2,6-(NO2)2 this pathway takes all the reaction flux. Copyright
Clay supported ammonium nitrate "clayan": A new reagent for selective nitration of arenes
Meshram,Ganesh,Madhavi,Eshwaraiah,Yadav,Gunasekar
, p. 2497 - 2503 (2007/10/03)
The nitration of activated, deactivated and highly functionalized arenes is described using clay-supported ammonium nitrate in the presence of perchloric acid.