cas 3279-07-0, 4-tert-Butyl-2-nitrophenol | Articles data

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Coumarin synthesis on π-acidic surfaces
Catalysis with anion-π interactions is emerging as an important topic in supramolecular chemistry. Among the reactions explored so far on π-acidic surfaces, coumarin synthesis stands out as a cascade process with several coupled anionic transition states. Increasing π-acidity has been shown in a different context to increase transition-state stabilisation and thus catalytic activity. In this report, we explore the possible use of macrocycles to accelerate coumarin synthesis between two π-acidic surfaces. To our disappointment, we found that compared to monomeric π-acids, coumarin synthesis within divalent macrocycles is clearly slower. Hindered access to an overly confined active site within the macrocycles could possibly account for this loss in activity, but several other explanations are certainly possible. However, operational coumarin synthesis on monomeric π-acidic surfaces is shown to tolerate structural modifications. Best results are obtained with structures that aim for proximity without obstructing transition-state stabilisation on the π-acidic surface.
Miros, Fran?ois N.,Huang, Guangxi,Zhao, Yingjie,Sakai, Naomi,Matile, Stefan
p. 303 - 309
(2015)
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Light-Controlled Tyrosine Nitration of Proteins
Tyrosine nitration of proteins is one of the most important oxidative post-translational modifications in vivo. A major obstacle for its biochemical and physiological studies is the lack of efficient and chemoselective protein tyrosine nitration reagents. Herein, we report a generalizable strategy for light-controlled protein tyrosine nitration by employing biocompatible dinitroimidazole reagents. Upon 390 nm irradiation, dinitroimidazoles efficiently convert tyrosine residues into 3-nitrotyrosine residues in peptides and proteins with fast kinetics and high chemoselectivity under neutral aqueous buffer conditions. The incorporation of 3-nitrotyrosine residues enhances the thermostability of lasso peptide natural products and endows murine tumor necrosis factor-α with strong immunogenicity to break self-tolerance. The light-controlled time resolution of this method allows the investigation of the impact of tyrosine nitration on the self-assembly behavior of α-synuclein.
Long, Tengfang,Liu, Lei,Tao, Youqi,Zhang, Wanli,Quan, Jiale,Zheng, Jie,Hegemann, Julian D.,Uesugi, Motonari,Yao, Wenbing,Tian, Hong,Wang, Huan
supporting information
p. 13414 - 13422
(2021/05/12)

Nitration method for aryl phenol or aryl ether derivative
The invention relates to a nitration method for an aryl phenol or aryl ether derivative. The method comprises the steps of stirring an aryl phenol or aryl ether compound, nitrate, trimethylchlorosilane (TMSCl) and a copper salt in an acetonitrile solution in air at room temperature, simultaneously, monitoring extent of reaction through a TLC dot plate, removing a solvent from a mixture by a rotaryevaporator after a substrate is consumed completely, and carrying out purification through a silica-gel column, thereby obtaining a nitroolefin derivative. Meanwhile, the selective mono-nitration orbis-nitration of the substrate can be achieved through controlling equivalent weight of the nitrate. Compared with the prior art, the nitration method disclosed by the invention has the advantages that the consumption of strong-acid substances is avoided, the reaction conditions are mild, the yield is high, the applicable range of the substrate is wide, reaction activity is free of obvious attenuation after an amplified reaction, and an excellent yield is still obtained, so that the method has an obvious industrial application value.
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Paragraph 0050-0055; 0071-0073

(2020/01/03)

Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Br?nsted Acidic NO2+ Generation
The first catalytic procedure for the electrophilic nitration of phenols was developed using iodosylbenzene as an organocatalyst based on iodine(III) and aluminum nitrate as a nitro group source. This atom-economic protocol occurs under mild, non-Br?nsted acidic and open-flask reaction conditions with a broad functional-group tolerance including several heterocycles. Density functional theory (DFT) calculations at the (SMD:MeCN)Mo8-HX/(LANLo8+f,6-311+G) level indicated that the reaction proceeds through a cationic pathway that efficiently generates the NO2+ ion, which is the nitrating species under neutral conditions.
Juárez-Ornelas, Kevin A.,Jiménez-Halla, J. Oscar C.,Kato, Terumasa,Solorio-Alvarado, César R.,Maruoka, Keiji
supporting information
p. 1315 - 1319
(2019/03/07)

Research on unique masked ortho-benzoquinone, monohemiaminal: Synthesis and reactions
Synthesis of ortho-benzoquinone monohemiaminals via the oxidative dearomatization/O-cyclization cascades of phenols bearing an ortho substituent derived from an amino alcohol with PIDA is described. The cascade reactions of substrates bearing a chiral substituent were found to proceed in a stereoselective manner. The Diels-Alder reactions of the ortho-benzoquinone monohemiaminals proceed in a highly stereoselective manner. The oxidative dearomatization/O-cyclization cascade affording the ortho-benzoquinone monohemiaminal had never been reported; hence, there is still ample scope for further investigation.
Matsumoto, Yuri,Nakamura, Akihiko,Saito, Emi,Nakada, Masahisa
p. 232 - 252
(2019/04/27)

Room-Temperature, Water-Promoted, Radical-Coupling Reactions of Phenols with tert -Butyl Nitrite
A radical-radical cross-coupling reaction of phenols with tert -butyl nitrite has been developed with the use of water as an additive. This method allows the construction of C-N bonds under an air atmosphere at room temperature, providing the ortho -nitrated phenol derivative in moderate to good yields.
Wei, Wen-Ting,Zhu, Wen-Ming,Liang, Weida,Wu, Yi,Huang, Hui-Yan,Huang, Yi-Ling,Luo, Junfei,Liang, Hongze
supporting information
p. 2153 - 2156
(2017/09/26)

A ortho-nitro phenol and its derivative synthesis method (by machine translation)
The invention relates to a method for the synthesis of organic compounds, in the existing technology of O-nitrophenol strong acid used in the synthesis process of the serious problem of environmental pollution and the synthesis step longer more complicated problem, the invention provides a ortho-nitro phenol and synthetic method of derivative thereof, proceeding by the phenol compound, synthesis of 2 - (phenoxy) pyridine, the obtained product, catalyst, tert-butyl nitrite, organic solvent and adding sealing in the pressure containers, in oil bath heating 50 - 100 °C, reaction 10 - 30 hours, to obtain 2 - (2 - nitrobenzene) ethoxy pyridine; re-processing by the ortho-nitro phenol and its derivatives; the method is simple, high-efficiency. (by machine translation)
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(2017/08/23)

An ortho-nitro phenol synthetic method of compound
The invention relates to a synthesis method of o-nitrophenol compounds, solving the problems that production hazards are easily caused due to the release of a large deal of heat during the synthesis of o-nitrophenol and the severe environment pollution caused due to the generation of a large deal of waste gas and acid in the process in the prior art. The invention provides the synthesis method of the o-nitrophenol compounds, which comprises the steps: synthesizing 2-(phenoxy)pyridine from phenol compounds; and then sequentially adding 2-(phenoxy)pyridine and a catalyst, a nitrating reagent, an oxidant and an organic solvent into a sealed pressure container, heating and reacting for 10-50 hours in an oil bath of which the temperature is 80 DEG C-130 DEG C to obtain 2-(2-nitrophenyl)oxy pyridine; and finally treating to obtain o-nitrophenol. The synthesis method is simple, convenient and efficient.
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(2016/10/10)

Palladium-catalyzed aromatic C-H bond nitration using removable directing groups: Regiospecific synthesis of substituted o -nitrophenols from related phenols
A general and regiospecific transformation of substituted phenols into the related o-nitrophenols has been achieved via a three-step process involving the palladium-catalyzed chelation-assisted ortho-C-H bond nitration as the key step. In the process, 2-pyridinyloxy groups act as removable directing groups for the palladium-catalyzed ortho-nitration of substituted 2-phenoxypridines, and they can be readily removed in the subsequent conversion of the resulting 2-(2-nitrophenoxy)pyridines into 2-nitrophenols.
Zhang, Wei,Zhang, Jian,Ren, Shaobo,Liu, Yunkui
p. 11508 - 11516
(2015/01/09)

Green and controllable metal-free nitrification and nitration of arylboronic acids
A novel and green nitrating reagent has been developed for the nitrification and nitration of arylboronic acids, which can be controlled by the reaction conditions. The process provides an attractive alternative to the traditional nitration protocols.
Wang, Shuai,Shu, Chun Chun,Wang, Tao,Yu, Jian,Yan, Guo Bing
scheme or table
p. 643 - 646
(2012/08/07)

A new method for the mononitration of phenol derivatives by poly(4-vinylpyridinium nitrate) and silica sulfuric acid under mild conditions
This procedure works efficiently for high selective mono nitration of phenol and substituted phenol to corresponding nitro compounds in moderate to high yield using poly(4-vinylpyridinium nitrate) and silica sulfuric acid in dichloromethane at room temperature.
Goudarziafshar, Hamid
experimental part
p. 458 - 461
(2012/06/18)

HARMFUL ARTHROPOD CONTROL COMPOSITION, AND FUSED HETEROCYCLIC COMPOUND
Disclosed is a harmful arthropod control composition comprising, as an active ingredient, a fused heterocyclic compound represented by formula (1) [wherein A1 and A2 independently represent a nitrogen atom or the like; R1 and R4 independently represent a halogen atom or the like; R2 and R3 independently represent a halogen atom or the like; R5 and R6 independently represent a linear C1-C6 hydrocarbon group which may be substituted, or the like (provided that both R5 and R6 cannot represent a hydrogen atom simultaneously); and n represents 0 or 1]. The harmful arthropod control composition has an excellent efficacy to control harmful arthropods.
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Page/Page column 121

(2011/02/18)

HARMFUL ARTHROPOD CONTROL COMPOSITION, AND FUSED HETEROCYCLIC COMPOUND
Disclosed is a harmful arthropod control composition comprising, as an active ingredient, a fused heterocyclic compound represented by formula (1) [wherein A1 and A2 independently represent a nitrogen atom or the like; R1 and R4 independently represent a halogen atom or the like; R2 and R3 independently represent a halogen atom or the like; R5 and R6 independently represent a linear C1-C6 hydrocarbon group which may be substituted, or the like (provided that both R5 and R6 cannot represent a hydrogen atom simultaneously); and n represents 0 or 1]. The harmful arthropod control composition has an excellent efficacy to control harmful arthropods.
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Page/Page column 76

(2011/04/13)

COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS
The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and a neonicotinoid compound; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and a neonicotinoid compound to the arthropod pests or a locus where the arthropod pests inhabit; and so on.
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Page/Page column 201

(2011/04/25)

COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS
The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and a pyrethroid compound; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and a pyrethroid compound to the arthropod pests or a locus where the arthropod pests inhabit; and so on.
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Page/Page column 202

(2011/05/06)

COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS
The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and pyriproxyfen; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and pyriproxyfen to the arthropod pests or a locus where the arthropod pests inhabit; and so on.
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Page/Page column 200-201

(2011/05/06)

COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS
The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and pyridalyl; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and pyridalyl to the arthropod pests or a locus where the arthropod pests inhabit; and so on.
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Page/Page column 200-201

(2011/05/06)

COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS
The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and a diamide compound; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and a diamide compound to the arthropod pests or a locus where the arthropod pests inhabit; and so on.
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Page/Page column 205

(2011/05/06)

Highly efficient nitration of phenolic compounds using some nitrates and oxalic acid under solvent-free conditions
Nitrophenols can be obtained by direct nitration of phenols with some nitrates and oxalic acid at room temperature in moderate to high yields under solvent-free conditions. A small amount of water proved to be important in the initial period of the reaction.
Ji, Li,Qian, Chao,Liu, Mei-Xin,Chen, Xin-Zhi
experimental part
p. 101 - 103
(2011/07/29)

A mild procedure for the preparation of o-nitrophenols by nitro urea or ammonium nitrate in the presence of silica sulfuric acid (SiO 2-OSO3H)
A mixture of ammonium nitrate or nitro urea and silica sulfuric acid was found to be efficient and environmentally friendly nitrating media for the preparation of orto-nitro phenols in dichloromethane at room temperature. A mixture of ammonium nitrate or nitro urea and silica sulfuric acid was found to be efficient and environmentally friendly nitrating media for the preparation of orto-nitro phenols in dichloromethane at room temperature.
Ghorbani-Choghamarani, Arash,Nikoorazm, Mohsen,Goudarziafshar, Hamid,Naserifar, Zahra,Zamani, Parisa
experimental part
p. 731 - 734
(2011/11/12)

Mononitration of phenol derivatives by guanidinium nitrate and silica sulfuric acid under mild conditions
A mixture of guanidinium nitrate and silica sulfuric acid acts as mild and heterogeneous media for the efficient mono nitration of phenolic compounds in dichloromethane at room temperature.
Ghorbani-Choghamarani, Arash,Goudarziafshar, Hamid,Nikoorazm, Mohsen,Naseri, Zahra
experimental part
p. 1431 - 1434
(2012/06/01)

Aluminum nitrate and silica sulfuric acid as efficient nitrating media for the mononitration of phenols under mild and heterogeneous conditions
A variety of phenol derivatives were successfully nitrated via combination of Al(NO3)3-9H2O and silica sulfuric acid in the presence of wet SiO2 (50% w/w) in dichloromethane at room temperature with moderate-to-good yields.
Ghorbani-Choghamarani, Arash,Goudarziafshar, Hamid,Nikoorazm, Mohsen,Yousefi, Somaieh
experimental part
p. 1144 - 1147
(2009/10/23)

1,2,3-TRIAZOLE AMIDE DERIVATIVES AS INHIBITORS OF CYTOKINE PRODUCTION
Disclosed are compounds of formula (I), where Ar1, X, R3, R4, R5 and R6 are defined herein. The compounds of the invention inhibit production of cytokines and are thus useful for treating cytokine mediated diseases. Also disclosed are processes for preparing these compounds and pharmaceutical compositions comprising these compounds.
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Page/Page column 41

(2008/06/13)

Process for producing aromatic compound derivative by reaction of aromatic compound substituted with sulfamoyloxy, sulfinamoyloxy, or carbamoyloxy group, with nucleophilic agent
A process for producing a compound represented by the following formula (I), which includes causing a compound represented by formula (II) to react with a nucleophilic agent: wherein X represents a substituent; R1 represents an electron-withdrawing substituent having a Hammett σp constant of more than 0; m represents an integer of 1 to 5; R2 represents a substituent; n represents an integer of 0 to 4; and m + n is from 1 to 5; wherein R1, m, R2, and n each have the same meanings to those in formula (I); R3 and R4 each independently represent an alkyl, aryl, or heterocyclic group; and Z represents C=O or S(O)p, wherein p is 1 or 2.
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Page/Page column 27

(2008/06/13)

Highly efficient catalytic nitration of phenolic compounds by nitric acid with a recoverable and reusable Zr or Hf oxychloride complex and KSF
Phenolic compounds can be nitrated with 60% nitric acid (1.2 equiv.) in the presence of catalytic amounts of a Zr or Hf oxychloride complex and montmorillonite KSF to give the corresponding nitrated products in good yields in a heterogeneous catalytic system. The co-catalyst and montmorillon ite can be easily recovered and reused in the next batch of nitration. This is a practical process for the nitration of phenolic compounds in a clean way. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
Shi, Min,Cui, Shi-Cong,Yin, Wan-Po
p. 2379 - 2384
(2007/10/03)

New insights into the reactivity of nitrogen dioxide with substituted phenols: A solvent effect
Various alkyl-substituted phenols react readily with nitrogen dioxide (.NO2) in different solvents at room temperature. In all cases nitration is the major reaction and leads to the formation of mono- and dinitrophenols and 4-nitrocyclohexa-2,5-dienones from 2,4,6-tri-substituted phenols. Oxidation, dimerisation and, in one case, nitrosation are also observed. The reaction pathway followed changes according to the solvent and to the nature and the number of substituents on the phenolic ring. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Astolfi, Paola,Panagiotaki, Maria,Greci, Lucedio
p. 3052 - 3059
(2007/10/03)

Nitration of phenolic compounds by metal-modified montmorillonite KSF
The nitration of phenolic compounds with 60% nitric acid (1.2 equiv) has been carried out in the presence of metal-modified montmorillonite KSF, prepared from different metals (V, Mo, W; Sc, La, Yb, Eu, In, Bi, Ti, Zr, Hf) and KSF or nitric acid treated HKSF, as catalysts. These catalysts showed good stabilities and high catalytic activities in nitration process. In addition, these catalysts can be recovered easily and reused for many times in nitration. This process is an eco-safer and environment-benign way for clean synthesis of nitrated phenolic compounds.
Yin, Wan-Po,Shi, Min
p. 10861 - 10867
(2007/10/03)

Microwave assisted synthesis of 4-alkyl-2-([5-substituted-2-hydroxyphenyl]- iminomethyl)benzenols and their NMR characterization
Imines, 4-alkyl-2-([5-substituted-2-hydroxyphenyl]iminomethyl)-benzenols 1, have been obtained successfully in excellent yield from the corresponding aldehydes and amines by microwave irradiation. The resultant Schiff bases have been fully characterized by spectral data.
Sridharan,Muthusubramanian,Sivasubramanian
p. 416 - 419
(2007/10/03)

A New Method for Nitration of Phenolic Compounds
Phenolic compounds can be nitrated by 65% nitric acid in the presence of catalytic amounts of montmorillonite KSF and bismuth(III) nitrate to give the corresponding nitrated products in good yields in a heterogeneous phase. The co-catalyst of KSF and Bi(NO3)3 can be easily recovered and reused in the next batch of nitration.
Shi, Min,Cui, Shi-Cong
p. 1197 - 1202
(2007/10/03)

Metallocyclodextrin catalysts for hydrolysis of phosphate triesters
The copper complexes of 6A-(2-aminoethylamino)- and 6A-(3-aminopropylamino)-6A-deoxy-β-cyclodextrin catalyse the hydrolysis of 4-tert-butyl-2-nitrophenyl dimethyl phosphate, with kinc=3.1×10-2 and 2.3×10-2 s-1, and Kd=4.3×10-4 and 1.2×10-3 M, respectively, in 0.05 M pH 7.0 HEPES buffer at 298 K. This corresponds to rate accelerations of more than 95 000 and 70 000 times for reaction of the cyclodextrin-bound species.
Barr, Lorna,Easton, Christopher J.,Lee, Kitty,Lincoln, Stephen F.,Simpson, Jamie S.
p. 7797 - 7800
(2007/10/03)

Reactivity of nitrite with 2-chlorophenol, t-butyl phenol and resorcinol in mild acidic conditions
The influence of ionic strength, pH, oxygen, organic solvents and nitrite concentration on the kinetics and the regioselectivity of 2-chlorophenol nitration by nitrous acid to form 4-nitro and 6-nitro derivatives was studied. There was quantitative para substitution at pH 3.5 in the absence of oxygen using 3 equiv of nitrite. In acetate-buffered solution, 4-t-butylphenol gave 90% 2-nitro-4-t-butylphenol, and resorcinol gave 85% 2,4-dinitrosoresorcinol. Nitration proceeded via nitrosation followed by oxidation of the nitroso intermediate into the corresponding nitro derivative. Oxidation could be due to reduction of nitrous acid to nitric oxide. The possibility that the reaction proceeds via radical formation, with which NO2 and NO interfere, is discussed. Elsevier,.
De La Breteche, Marie-Laure,Billion, Marie-Annick,Ducrocq, Claire
p. 973 - 977
(2007/10/03)

Hydrocarbons and chloroaromatics from anilines and n-butyl nitrite
A single reagent, i.e. n-butyl nitrite, can be used to oxidize an aromatic amine, or the corresponding N-methylene derivative, to a diazo compound followed by its subsequent reduction to hydrocarbon in a single batch.Alternatively, a chloro derivative can be obtained if carbon tetrachloride is used as the solvent.The reactions appear to be general and complete product identification was accomplished.
Giumanini, Angelo G.,Verardo, Giancarlo,Gorassini, Fausto,Strazzolini, Paolo
p. 311 - 316
(2007/10/02)

MONONITRATION DE PHENOLS PAR DES NITRATES METALLIQUES
A new and practical route to mononitrphenol in high yields is described using commercially aviable hydrated metallic nitrates.According to the metallic nitrate used, this reaction can yield regiospecifically the ortho-nitrophenol or regioselectively the para-nitrophenol.This method is successfully applied to some phenolic derivatives, in particular to the preparation of 2-nitroestrone.Sodium nitrate with ferric chloride or with titane tetrachloride allows mononitration of phenol.
Poirier, Jean-Marie,Vottero, Catherine
p. 1415 - 1422
(2007/10/02)

NITRATION OF PHENOLS BY CLAY-SUPPORTED FERRIC NITRATE
"Clayfen", a reactive form of ferric nitrate stabilized by adsorption unto an acidic K 10 clay, is an efficient and selective nitrating agent of phenols, under very mild conditions.It leads specifically to mononitration, with high regioselectivities.These characteristics, coupled with its low cost, ease of preparation and the simplicity of experimental procedures, make "clayfen" an attractive nitrating reagent.
Cornelis, A.,Laszlo, P.,Pennetreau, P.
p. 961 - 972
(2007/10/02)