cas 7244-78-2, 4-N-BUTOXYNITROBENZENE | Articles data

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Ultrasound assisted the preparation of 1-butoxy-4-nitrobenzene under a new multi-site phase-transfer catalyst - Kinetic study
In the present research work deals with the preparation of 1-butoxy-4-nitrobenzene was successfully carried out by 4-nitrophenol with n-butyl bromide using aqueous potassium carbonate and catalyzed by a new multi-site phase-transfer catalyst (MPTC) viz.,
Harikumar, Kuppuswamy,Rajendran, Venugopal
p. 208 - 215
(2014)
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Aryl Ether Syntheses via Aromatic Substitution Proceeding under Mild Conditions
In this study, mild conditions for aromatic substitutions during the syntheses of aryl ethers were developed. In the reaction conditions, the choices of solvent, base, and the sequence for the addition of the reagents proved important. A wide variety of alcohols were used directly as nucleophiles and smoothly reacted with aryl chlorides that possessed either a nitro or a cyano group at either the ortho- or para-position. Controlled experiments we performed suggested that the reaction underwent a charge-transfer process mediated by a combination of DMF and tert-BuOK.
Ando, Shin,Tsuzaki, Marina,Ishizuka, Tadao
p. 11181 - 11189
(2020/10/12)

Synthesis and antimicrobial studies of new antibacterial azo-compounds active against staphylococcus aureus and listeria monocytogenes
Some novel (phenyl-diazenyl)phenols (4a–m) were designed and synthesized to be evaluated for their antibacterial activity. Starting from an active previously-synthesized azobenzene chosen as lead compound, we introduced some modifications and optimization of the structure, in order to improve solubility and drug conveyance. Structures of all newly-synthesized compounds were confirmed by 1H nuclear magnetic resonance (NMR), mass spectrometry, and UV-Vis spectroscopy. Antibacterial activity of the new compounds was tested with the dilution method against the bacteria strains Listeria monocytogenes, Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa PAO1. All the compounds were selectively active against Gram-positive bacteria. In particular, compounds 4d, 4h, and 4i showed the highest activity against S. aureus and Listeria monocytogenes, reaching remarkable MIC100 values of 4 μg/mL and 8 μg/mL. The relationship between antimicrobial activity and compound structure has suggested that the presence of hydroxyl groups seems to be essential for antimicrobial activity of phenolic compounds.
Piotto, Stefano,Concilio, Simona,Sessa, Lucia,Diana, Rosita,Torrens, Gabriel,Juan, Carlos,Caruso, Ugo,Iannelli, Pio
(2017/08/29)

Liquid-crystalline polymorphism of 4-heptyloxybenzylidene-4′- alkyloxyanilines and their phase equilibrium with 4-octyloxyphenyl 4-nitrobenzoate
This paper describes the synthesis and liquid-crystalline properties of the homologous series of 4-heptyloxybenzylidene-4′-alkyloxyanilines (7-n). Six of them are presented for the first time. Based on the polarization microscopy (POM and TOA methods) and the calorimetric (DSC) measurements following polymorphism has been detected: nematic, smectic C and smectic I mesophases. The presence of these mesophases was confirmed by the miscibility method, using 4-octyloxyphenyl 4-nitrobenzoate and terephtal-bis (4-butyloaniline) as a mesophase references. Extraordinary results have been found in the mixtures of the investigated compounds with 4-octyloxyphenyl 4-nitrobenzoate; Induced smectic A has been observed, which is connected with very strong intermolecular interactions. Additionally destabilization of nematic and smectic C phases was visible.
Godzwon, Joanna,Sienkowska, Monika J.,Galewski, Zbigniew
scheme or table
p. 75 - 82
(2012/04/04)

Alkoxylation of 4-chloronitrobenzene with aliphatic alcohols and glycols in the presence of NaOH
The reaction of 4-chloronitrobenzene with aliphatic C1-n-C 4 alcohols and with mono-, di-, and triethylene glycols in the presence of NaOH in liquid ammonia at 15-50°C was studied.
Malykhin, E. V.,Shteingarts, V. D.
p. 1232 - 1238,7
(2020/09/09)

Novel supramolecular organocatalysts of hydroxyprolinamide based on calix[4]arene scaffold for the enantioselective Biginelli reaction
A series of novel supramolecular organocatalysts of hydroxyprolinamide based on the upper rim of calix[4]arene scaffold have been developed to catalyze enantioselective multi-component Biginelli reaction. Under the optimal conditions, the reactions occurred with moderate-to-excellent enantioselectivities (up to 98% ee). A plausible transition state constructed by the supramolecular interaction of hydrogen bond and cation-π between catalysts and substrates has been proposed.
Li, Zhengyi,Xing, Huaijie,Huang, Guoli,Sun, Xiaoqiang,Jiang, Juli,Wang, Leyong
experimental part
p. 1726 - 1734
(2012/04/18)

Bis(μ-iodo)bis[(-)-sparteine]-dicopper: A versatile catalyst for direct O-Arylation and O-Alkylation of phenols and aliphatic alcohols with haloarenes
The easy to prepare dimeric bis(μ-iodo)bis[(-)-sparteine]- dicopper ([CuI{(-)-spa}]2 complex) is shown to be versatile catalyst for O-arylation and O-alkylation with various aryl halides with phenols and aliphatic alcohols respectively, including less reactive aryl chlorides, such as chlorobenzene under mild conditions.
Satyanarayana, Ponnam,Maheswaran, Hariharasarma,Kantam, Mannepalli Lakshmi,Bhargava, Suresh
supporting information; experimental part
p. 788 - 790
(2011/08/22)

Novel Prolinamide Organocatalysts Based on Calix[4]arene Scaffold for the Enantioselective Direct Aldol Reaction
A series of novel prolinamide organocatalysts based on calix[4]arene scaffold have been developed to catalyze the direct asymmetric aldol reaction of aromatic aldehydes and cyclohexanone. Under the optimal condition, high isolated yields (up to 99%) and enantioselectivities (up to 97% ee), and moderate diastereoselectivities (up to 85/15) were obtained.
Li, Zheng-Yi,Lu, Cheng-Xi,Huang, Guoli,Ma, Jie-Jie,Sun, Hongsheng,Wang, Leyong,Pan, Yi
scheme or table
p. 461 - 466
(2011/09/14)

Synthesis of alkyl-aryl ethers by copper-catalyzed etherization reactions of aryl fluorides with tetraalkylammonium bromides and H2O
Synthesis of alkyl aryl ethers via copper-catalyzed etherizations of electron-deficient aryl fluorides with quaternary ammonium bromides and water has been developed. In the presence of Cu(OAc)2, POPh3 (L4) and Cs2CO3, a variety of electron-deficient aryl fluorides underwent the reaction with quaternary ammonium bromides and H 2O in moderate to good yields. The mechanism was also discussed. Synthesis of alkyl aryl ethers via copper-catalyzed etherizations of electron-deficient aryl fluorides with quaternary ammonium bromides and water has been developed. In the presence of Cu(OAc)2, POPh3 (L4) and Cs2CO3, a variety of electron-deficient aryl fluorides underwent the reaction with quaternary ammonium bromides and H 2O in moderate to good yields. Copyright
Wang, Feng,Tang, Boxiao,Xie, Yexiang,Li, Jinheng
experimental part
p. 2318 - 2322
(2011/10/03)

Fused ring compound and use thereof
The present invention provides a compound represented by the formula: wherein the symbols are as described in the specification, or a salt thereof, which is useful for preventing/treating eicosanoid-associated diseases such as atherosclerosis, diabetes, obesity, atherothrombosis, asthma, fever, pain, cancer, rheumatism, osteoarthritis and atopic dermatitis, and which has an excellent pharmacological action, physicochemical properties, etc.
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(2010/08/07)

Copper(I)-catalyzed aryl bromides to form intermolecular and intramolecular carbon-oxygen bonds
(Chemical Equation Presented) A highly efficient Cu-catalyzed C-O bond-forming reaction of alcohol and aryl bromides has been developed. This transformation was realized through the use of copper(I) iodide as a catalyst, 8-hydroxyquinoline as a ligand, and K3PO4 as a base. A variety of functionalized substrates were found to react under these reaction conditions to provide products in good to excellent yields.
Niu, Jiajia,Guo, Pengran,Kang, Juntao,Li, Zhigang,Xu, Jingwei,Hu, Shaojing
supporting information; experimental part
p. 5075 - 5078
(2009/10/17)

One-dimensional to three-dimensional electronic conduction in liquid crystalline mesophases
We have established the electronic conduction in the nematic phase of a small molecule of a 2-phenylbenzothiazole derivative, i.e., 2-(4'- octyloxyphenyl)-6-butoxybenzothiazole (8O-PBT-O4). This gives a new insight into the quest for the electronic conduction in liquid crystals, which was initiated by Kusabayashi and Labes in late 1960s and had succeeded over several decades, leading it to the end. In addition, it is clarified that the ionic conduction often observed in less ordered mesophases is induced with trace amounts of chemical impurities due to its low viscosity. The present result indicates that the charge carrier transport in the mesophase is electronic in its intrinsic nature irrespective of mesophases and molecular sizes, i.e., 1D-electronic conduction in columnar phase, 2D-electronic conduction in smectic mesophases, and 3D-electronic conduction in the nematic phase.
Tokunaga, Keiji,Takayashiki, Yukiko,Iino, Hiroaki,Hanna, Jun-Ichi
scheme or table
p. 250 - 258
(2010/06/15)

Charge carrier transport properties in liquid crystalline 2-phenylbenzothiazole derivatives
We synthesized liquid crystalline 2-phenylbenzothiazole derivatives and investigated their charge carrier transport properties by time-of-flight experiments. These materials show less ordered phases such as smectic A, smectic C, and nematic phases at temperature range lower than 100°C, and their mobility was relatively small, from 10-5cm2/Vs to 10 -4cm2/Vs. In addition, the mobility depends on temperature, while it did not depend on electric fields. According to these results, we estimated the eneregy distribution of density of states responsible for condition, σ of Gaussian width, to be 78 ～ 118meV.
Tokunaga, Keiji,Iino, Hiroaki,Hanna, Jun-Ichi
scheme or table
p. 241 - 249
(2010/06/16)

An efficient intermolecular BINAM-copper(I) catalyzed Ullmann-type coupling of aryl iodides/bromides with aliphatic alcohols
A wide range of alkyl aryl ethers are synthesized from the corresponding aryl iodides and aliphatic alcohols through Ullmann-type intermolecular coupling reactions in the presence of a catalytic amount of easily available BINAM-CuI complex. Less reactive aryl bromides have also been shown to react with aliphatic alcohols under identical reaction conditions to give good yields of the alkyl aryl ethers without increasing the reaction temperature and time.
Naidu, Ajay B.,Sekar
p. 3147 - 3151
(2008/09/20)

Smectic polymorphism of 4-nonyloxybenzylidene-4′-alkyloxyanilines
This paper describes liquid-crystalline polymorphism of the homologous series of 4-nonyloxybenzylidene-4′-alkyloxyanilines. Based on the polarization microscopy (POM, TOA) and the calorimetric (DSC) measurements the following mesophases were detected: nematic, smectic A, smectic C, smectic B, smectic I and smectic G. The presence of these mesophases was confirmed by the miscibility method, using: 4-heptyloxybenzilidene-4′-pentylaniline, 4-hexyl-4′-decyloxyazobenzene and 4-nonyloxybenzilidene-4′-butylaniline as mesophase references. Influence of the alkyl chain length on the type of mesophases and entropic effects of phase transition are discussed.
Godzwon, Joanna,Sienkowska, Monika J.,Galewski, Zbigniew
p. 259 - 267
(2008/03/13)

Solvatochromic properties of long alkyl chain π* indicators: Comparison of N/N-dialkyl-4-nitroanilines and alkyl 4-nitrophenyl ethers
Hydrophobic forms of the N/N-dialkyl-4-nitroaniline (DNAP) (p-O 2NC6H4NR2) (1a-f) and alkyl-4-nitrophenyl ether (p-O2NC6H4OR) (2a-c) solvatochromic π* indicators have been charac
Helburn,Bartoli,Pohaku,Maxka,Compton,Creedon,Stimpson
p. 321 - 331
(2008/02/03)

An efficient lutidine-assisted etherification of phenols with alkyl chloride in water
An efficient etherification of phenol derivatives with alkyl chloride in water was achieved. The reactivity of the ether bond forming reaction was activated by addition of 2,6-lutidine.
Aki, Shinji,Nishi, Takao,Minamikawa, Jun-Ichi
p. 940 - 941
(2007/10/03)

The newborn surface of dull metals in organic synthesis. Bismuth-mediated solvent-free one-step conversion of nitroarenes to azoxy- and azoarenes
When milled together with bismuth shots, nitroarenes are readily converted to azoxy- and/or azoarenes depending on substrates and conditions employed. Simple extraction with organic solvent followed by evaporation of the resulting dark pasty solid gave the product in good yield.
Wada, Shinobu,Urano, Mika,Suzuki, Hitomi
p. 8254 - 8257
(2007/10/03)

Liquid crystalline properties of azobenzenes: I. 4-methoxy-, 4-ethoxy-, 4-propoxy-and 4-butoxy-4′-alkyloxyazobenzenes
Liquid crystalline properties of four series of azobenzenes, 4-methoxy-4-alkyloxyazobenzenes (azo-1-n), 4-ethoxy-4′-alkyloxyazobenzenes (azo-2-n), 4-propoxy-4′al-kyloxyazobenzenes (azo-3-n) and 4-butoxy-4′-alkyloxyazobenzenes (azo-4-n), were investigated. By polarizing microscopy nematic and smectic C mesophases were detected. By DSC and TOA thermo-optics the parameters of phase transitions were measured. A typical odd-even effect of the clearing temperature was found. No smectic phase was detected in the first three series, even for the longest alkyloxy chains. The smectic C appears for the first time in the butoxy family, starting from the undecyloxyl derivative. In each series a polymorphism in the solid state was detected, especially significant in the propoxy and butoxy family, that was explained in terms of the ODIC phases.
Galewski,Hofmanska,Zielinska
p. 1357 - 1371
(2007/10/03)

Mesogenic properties of liquid crystals having a chiral semiflexible joint
Two homologous series of mesogenic enantiomers with chiral semiflexible joint, -C*H(CH3)CH2COO-, are examined. High twist power and presence of blue phases with short lattice period are found for eleven examined compounds. Some effects of chirality in reentrant system are discussed. On phase diagram of enantiomers the SmAd phase area is shifted toward longer homologues as compared to racemates. In result, an island of the SmAd phase in the cholesteric sea exists on binary phase diagrams of R- and S- enantiomers. Triple divergence of the pitch in the cholesteric phase of a pure compound is observed.
Gorecha,Pyzuk,Mieczkowski
p. 33 - 42
(2007/10/02)

Kinetics of Phase-transfer Etherification Reactions of p-Chloronitrobenzene by Alkoxides
The substitution reaction of chloride by alkoxide anions in p-chloronitrobenzene in a phase-transfer catalytic system has been studied and succesfully performed in high yield and without the occurrence of side reactions.The effect of several parameters has been experimentally investigated.In particular, the poisoning effect of the chloride anion produced throughout the reaction is studied and a practical answer to succesfully overcome this problem and increase yields is presented.A kinetic model based on the collected data is proposed.
Lerner, Jaime de la Zerda,Cohen, Sasson,Sasson, Yoel
p. 1 - 6
(2007/10/02)

The Influence of Water Traces on Some Liquid/Solid Phase Transfer Catalysis Processes (Applications of Phase Transfer Catalysis, Part 42)
Rates of solid/liquid phase transfer catalytic conversions (an ester formation, an ether formation, a cyanide displacement, and a dichlorocarbene generation) were investigated using onium salts and dicyclohexano-18-crown-6 as catalysts and varying the (very low) water content of the system.The influence of the water traces varies strongly with the types of anions and catalysts.
Dehmlow, Eckehard V.,Raths, Hans-Christian
p. 2901 - 2917
(2007/10/02)

The effect of the phosphoryl group on the rate and mechanism of SN-substitution at the saturated carbon atoms
The reactivity of diarylphosphine oxides RR'P(O)CH2X with p-O2NC6H4ONa in DMF have been studied.The reaction rate increases with the electrodrawing properties of the substituents on R and R' in the following way: p-Me2NC6H4 2 reaction rate of diphenylphosphine oxides has been investigated.The reactivity increases as follows Cl I Br OTs.A reaction mechanism is suggested.
Tsvetkov, E. N.,Tkachenko, S. E.,Yarkevich, A. N.
p. 339 - 341
(2007/10/02)

NUCLEOPHILIC SUBSTITUTION OF CHLORINE ATOM IN DIARYL CHLOROMETHYLPHOSPHINE OXIDES
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Yarkevich, A. N.,Tkachenko, S. E.,Tsvetkov, E. N.
p. 1430 - 1435
(2007/10/02)

Comparative Structure-Activity Relationships of Antifolate Triazines Inhibiting Murine Tumor Cells Sensitive and Resistant to Methotrexate
The inhibitory effect of 108 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(substituted-phenyl)-s-triazines on murine L5178Y tumor cells, resistant and sensitive to methotrexate (MTX), has been studied.From the pI50 values, quantitative structure-activity relationships have been formulated which show that the lipophilic triazines are much more inhibitory against resistant cells than methotrexate or hydrophilic triazines.The results are compared with the behavior of other antifolate drugs that have been used in chemotherapy, as well as with eight antitumor drugs that are notantifolates.The acquired resistance of these cells toward hydrophilic antifolates may be attributed to the combined effect of an impaired active-transport system, a change in the conformation of dihydrofolate reductase in the resistant cells, and an amplified production of dihydrofolate reductase in the resistant cells.
Selassie, Cynthia Dias,Hansch, Corwin,Khwaja, Tasneem A.,Dias, Cecilia B.,Pentecost, Stephanie
p. 347 - 357
(2007/10/02)

Anion Activation in the Synthesis of Ethers from Oxygen Anions and 1-Chloro-4-nitrobenzene
Reactions of 1-chloro-4-nitrobenzene (1) with alkoxide ions in the parent alcohols do not afford satisfactory yields of the expected alkyl 4-nitroaryl ether except in the case of the short-chain primary alcohols.We report that in the model reaction of 1 with KOH in 2-propanol good yields of 1-isopropoxy-4-nitrobenzene (2) are obtained provided Bu4NBr or alkali ion complexing agents such as 18-crown-6, Carbowax 20M, MPEG 5000, and Triton X-100 are present.Low molecular weight ethers, like glyme-5, are less effective, with ethylene glycol dimethyl ether having no effect at all.Work at temperatures below the solution boiling point is recommended to avoid competitive reduction of the NO2 group.The preparative value of Bu4NBr additions in analogous reactions of 1 to give 4-O2NC6H4OR ethers (3) is also very significant when R is primary, secondary, and aryl (1-octyl, sec-butyl, phenyl).The reaction fails when R = tert-butyl and 4-O2NC6H4.
Paradisi, Cristina,Quintily, Ugo,Scorrano, Gianfranco
p. 3022 - 3026
(2007/10/02)

NON-CATALYZED REDUCTIONS WITH FORMATE SALTS: CONVERSION OF NITROAROMATIC COMPOUNDS TO THE CORRESPONDING PRIMARY AMINES
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Babler, James H.,Sarussi, Steven J.
p. 925 - 930
(2007/10/02)

9-(P-phenylazoanilino)-7-methyl-1H-imidazo[4,5-f]quinolines
A series of 9-(substituted amino)imidazo[4,5-f]quinolines are effective anthelmintic agents; particularly in respect to the tapeworm Hymenolepis nana.
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(2008/06/13)