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16365-27-8

16365-27-8

Identification

  • Product Name:Ethanol,2-(4-nitrophenoxy)-

  • CAS Number: 16365-27-8

  • EINECS:

  • Molecular Weight:183.164

  • Molecular Formula: C8H9 N O4

  • HS Code:2909499000

  • Mol File:16365-27-8.mol

Synonyms:Ethanol,2-(p-nitrophenoxy)- (6CI,7CI,8CI); 2-((4-Nitrophenyl)oxy)ethanol;2-(4-Nitrophenoxy)ethanol; 2-(p-Nitrophenoxy)ethanol; 4-Nitro-(2-hydroxyethoxy)benzene;NSC 30512; NSC 47172; b-Hydroxyethyl p-nitrophenyl ether

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  • Hazard Codes:Xi

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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2-(4-Nitrophenoxy)ethanol ≥97.0% (HPLC)
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:2-(p-Nitrophenoxy)ethanol
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Relevant articles and documentsAll total 47 Articles be found

Molecular rulers: New families of molecules for measuring interfacial widths

Steel, William H.,Damkaci, Fehmi,Nolan, Ryan,Walker, Robert A.

, p. 4824 - 4831 (2002)

Homologous series of solvatochromic neutral alcohols and ionic sulfates are synthesized and characterized. Each surfactant series consists of hydrophobic, p-nitroanisole-based chromophores attached to polar or ionic headgroups by n-alkyl spacers. UV absorption measurements show that the optical properties of surfactant chromophores closely track those of the parent chromophore. Interfacial tension measurements are used to calculate surface excess concentrations of ionic surfactants adsorbed to an aqueous-cyclohexane interface. With a hydrophobic chromophore, a hydrophilic headgroup, and a variable-length, alkyl spacer, these surfactants have the potential to function as molecular rulers: probes of molecular-scale variation in solvation forces across condensed-phase interfaces. Changing the separation between the hydrophobic, solvatochromic probe and the hydrophilic headgroup should enable different members of a homologous series to span different interfacial widths, thus exposing the chromophore to different chemical environments. This idea is explored by using surface-specific, nonlinear optical spectroscopy. Resonant second harmonic spectra of p-nitroanisole and the surfactant product 4a adsorbed to an aqueous-cyclohexane interface show the surfactant spectrum blue-shifted 9 nm relative to the spectrum of adsorbed p-nitroanisole. On the basis of chromophore solvatochromism, these results are consistent with a less polar environment surrounding the surfactant chromophore. Significant differences in interfacial solvation resulting from a ~5 A separation between the surfactant headgroup and chromophore support recently proposed models of molecularly sharp, microscopically flat aqueous-alkane interfaces.

Design, synthesis, biological evaluation and molecular docking studies of novel 3-aryl-4-anilino-2H-chromen-2-one derivatives targeting ERα as anti-breast cancer agents

Luo, Guoshun,Chen, Mingqi,Lyu, Weiting,Zhao, Ruheng,Xu, Qian,You, Qidong,Xiang, Hua

, p. 2668 - 2673 (2017)

The estrogen receptor (ER) has played an important role in breast cancer development and progression and is a central target for anticancer drug discovery. In order to develop novel selective ERα modulators (SERMs), we designed and synthesized 18 novel 3-aryl-4-anilino-2H-chromen-2-one derivatives based on previously reported lead compounds. The biological results indicated that most of the compounds presented potent ERα binding affinity and possessed better anti-proliferative activities against MCF-7 and Ishikawa cell lines than the positive control tamoxifen. The piperidyl substituted compounds such as 16d and 18d demonstrated strong ERα binding affinities and excellent anti-proliferative activities respectively. Compound 18d displayed the most potent ERα binding affinity with RBA value of 2.83%, while 16d exhibited the best anti-proliferative activity against MCF-7 cells with IC50 value of 4.52?±?2.47?μM. Further molecular docking studies were also carried out to investigate binding pattern of the newly synthesized compounds with ERα. All these results together with the structure–activity relationships (SARs) indicated that these 3-aryl-4-anilino-2H-chromen-2-one derivatives with basic side chain could serve as promising leads for further optimization as novel SERMs.

Solvent polarity across weakly associating interfaces

Steel, William H.,Lau, Yuen Y.,Beildeck, Carmen L.,Walker, Robert A.

, p. 13370 - 13378 (2004)

Molecular ruler surfactants, solvatochromic probes of solvent polarity, have been used to examine changes in solvent polarity across weakly associating liquid/liquid interfaces. The water/alkane interfaces were formed between an aqueous subphase and either cyclic (cyclohexane and methylcyclohexane) or linear (octane and hexadecane) alkanes. Resonance-enhanced second-harmonic generation was used to collect effective excitation spectra of species adsorbed to these interfaces. As surfactants lengthened, the surfactant probe sampled an increasingly nonpolar environment as evidenced by an excitation wavelength that shifted toward the alkane limit. Data suggest that all four water/alkane interfaces are molecularly sharp (9 Aì?), but that differences in the solvent molecular structure alter the transition from aqueous to organic solvation across the interface. Polarity across two interfaces (cyclohexane and hexadecane) changes gradually over the distance spanned by ruler surfactants. In contrast, the transitions at the interfaces between water and methylcyclohexane and octane appear much more abrupt. These findings appear to correlate with each organic solvent's ability to pack and associated free volume. More free volume in the organic phase leads to a more abrupt water/alkane interface. Results are interpreted on the basis of recent molecular dynamics simulations examining polarity at different water/monolayer interfaces.

COMPOUNDS TARGETING RNA-BINDING PROTEINS OR RNA-MODIFYING PROTEINS

-

Page/Page column 103; 104, (2021/09/11)

The invention relates to a compound represented by Formula (I): or a pharmaceutically acceptable salt thereof, compositions comprising the same and methods of preparing and using the same. The variables are described herein.

Synthetic and Mechanistic Studies on 2,3-Dihydrobenzo[ b ][1,4]-oxaselenines Formation from Selenocyanates

Bonesi, Sergio M.,Cattaneo, Mauricio,Chao, María N.,Rodriguez, Juan B.,Sanchez Gonzalez, Jonathan,Szajnman, Sergio H.

, p. 1643 - 1658 (2020/05/25)

An expedient preparation of selenium-containing hetero-cycles via an m -chloroperbenzoic acid-mediated seleno-annulation starting from selenocyanate derivatives is described. In spite of its significance, this cyclization reaction is virtually understudied not only from the point of view of its scope, but also from the mechanistic aspects associated to this remarkable transformation. In this sense, several selenocyanate and thiocyanate derivatives bearing an aromatic ring were evaluated as substrates under different reaction conditions of this interesting cyclization yielding important insights on its scope as well as relevant information on the reaction mechanism.

Further insights of selenium-containing analogues of WC-9 against Trypanosoma cruzi

Chao, María N.,Lorenzo-Ocampo, María V.,Szajnman, Sergio H.,Docampo, Roberto,Rodriguez, Juan B.

, p. 1350 - 1361 (2019/02/25)

As a continuation of our project aimed at searching for new chemotherapeutic agents against American trypanosomiasis (Chagas disease), new selenocyanate derivatives were designed, synthesized and biologically evaluated against the clinically more relevant dividing form of Trypanosoma cruzi, the etiologic agent of this illness. In addition, in order to establish the role of each part of the selenocyanate moiety, different derivatives, in which the selenium atom or the cyano group were absent, were conceived, synthesized and biologically evaluated. In addition, in order to study the optimal position of the terminal phenoxy group, new regioisomers of WC-9 were synthesized and evaluated against T. cruzi. Finally, the resolution of a racemic mixture of a very potent conformationally rigid analogue of WC-9 was accomplished and further tested as growth inhibitors of T. cruzi proliferation. The results provide further insight into the role of the selenocyanate group in its antiparasitic activity.

Design, synthesis, and biological evaluation of some novel 4-aminoquinazolines as Pan-PI3K inhibitors

Ding, Huai-Wei,Wang, Shu,Qin, Xiao-Chun,Wang, Jian,Song, Hong-Rui,Zhao, Qing-Chun,Song, Shao-Jiang

, p. 2729 - 2740 (2019/05/17)

A series of 4-aminoquinazolines derivatives containing hydrophilic group were designed and identified as potent Pan-PI3K inhibitors in this study. The results of antiproliferative assays in vitro showed that this series of compounds had strong inhibition of tumor growth, especially compound 7b for MCF-7 cells but weak inhibition to normal cells. PI3K kinase assay showed that 7b had high activity for three PI3K isoforms with the IC50 values of picomole. The western blot assay indicated that 7b could decrease the phospho-Akt (S473) in a dose-dependent manner. Further experiments showed that 7b could induce apoptosis in MCF-7 cells. Four key hydrogen bonding interactions were found in the docking of 7b with PI3K kinase. All these results suggested that 7b is a potent PI3K inhibitor and could be considered as a potential candidate for the development of anticancer agents.

Revisiting Hydroxyalkylation of Phenols with Cyclic Carbonates

Kao, Shih-Chieh,Lin, Yi-Ching,Ryu, Ilhyong,Wu, Yen-Ku

supporting information, p. 3639 - 3644 (2019/07/10)

Described is a tetrabutylammonium fluoride-mediated hydroxyalkylation reaction of phenols with cyclic carbonates. This operationally simple method enables the synthesis of a variety of aryl β-hydroxyethyl ethers in good to excellent yields with a very small amount of catalyst loading (0.1–1 mol%). Of particular note is the efficient conversion of aromatic diols and phloroglucinol to the corresponding bis- and tris-hydroxyethylated products. To further showcase the versatility of this protocol, guaifenesin was prepared with a single step by the condensation of guaiacol and glycerol carbonate. We also developed a flow ethoxylation process permitting the continuous synthesis of multiflorol. (Figure presented.).

Process route upstream and downstream products

Process route

ethylene glycol
107-21-1

ethylene glycol

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

2-(4-nitrophenoxy)ethanol
16365-27-8

2-(4-nitrophenoxy)ethanol

1,2-bis(4-nitrophenoxy)ethane
14467-69-7

1,2-bis(4-nitrophenoxy)ethane

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

Conditions
Conditions Yield
With ammonia; sodium hydroxide; at 15 ℃; for 15h; Autoclave;
9.4%
4 g
0.4 g
2.8 g
4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

2-(4-nitrophenoxy)ethanol
16365-27-8

2-(4-nitrophenoxy)ethanol

2-(4-aminophenoxy)ethanol
6421-88-1

2-(4-aminophenoxy)ethanol

Conditions
Conditions Yield
With sodium carbonate; In ethylene glycol;
2-bromoethanol
540-51-2

2-bromoethanol

2-(4-nitrophenoxy)ethanol
16365-27-8

2-(4-nitrophenoxy)ethanol

Conditions
Conditions Yield
With potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 12h;
97.2%
4-nitro-phenol; With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 6h; Inert atmosphere;
2-bromoethanol; In N,N-dimethyl-formamide; at 50 ℃; for 24h; Inert atmosphere;
88.6%
4-nitro-phenol; With potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 1h;
2-bromoethanol; In N,N-dimethyl-formamide; at 20 - 80 ℃; for 6.33333h;
67%
With potassium carbonate; In N,N-dimethyl-formamide; at 90 ℃; for 18h;
67%
With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃;
67.6%
With potassium carbonate; In butanone; for 8h; Reflux;
61%
With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 90 ℃; for 16h;
With potassium carbonate; In acetone;
With sodium hydroxide; In water; at 85 ℃; for 7h;
2-chloro-ethanol
107-07-3

2-chloro-ethanol

2-(4-nitrophenoxy)ethanol
16365-27-8

2-(4-nitrophenoxy)ethanol

Conditions
Conditions Yield
With potassium carbonate; In dimethyl sulfoxide; at 60 ℃; for 6h;
80%
4-nitro-phenol; With sodium methylate; In 1-methyl-pyrrolidin-2-one; at 100 ℃; under 60.006 Torr;
2-chloro-ethanol; In 1-methyl-pyrrolidin-2-one; at 120 ℃; for 3h;
27%
4-nitro-phenol; With sodium methylate; In 1-methyl-pyrrolidin-2-one; at 100 ℃; under 60.006 Torr;
2-chloro-ethanol; at 120 ℃; for 3h;
27%
With sodium methylate; In 1-methyl-pyrrolidin-2-one; at 120 ℃; for 3h;
27%
4-nitro-phenol; With sodium methylate; In 1-methyl-pyrrolidin-2-one; at 100 ℃; under 60.006 Torr;
2-chloro-ethanol; at 120 ℃; for 3h;
27%
4-nitro-phenol; With sodium methylate; In 1-methyl-pyrrolidin-2-one; at 100 ℃; under 60.006 Torr;
2-chloro-ethanol; In 1-methyl-pyrrolidin-2-one; at 120 ℃; for 3h;
27%
With sodium hydroxide;
With sodium hydroxide; In methanol; water; N,N-dimethyl-formamide;
21.62 g (92%)
4-nitro-phenol; With potassium hydroxide; In water;
2-chloro-ethanol; In water;
With sodium hydroxide; at 20 ℃;
With sodium hydroxide; In water; at 20 ℃; for 24h; Inert atmosphere;
With sodium hydroxide; In water; at 80 ℃; for 8h; Inert atmosphere;
ethylene glycol
107-21-1

ethylene glycol

4-Fluoronitrobenzene
350-46-9,178603-76-4

4-Fluoronitrobenzene

2-(4-nitrophenoxy)ethanol
16365-27-8

2-(4-nitrophenoxy)ethanol

Conditions
Conditions Yield
With potassium carbonate; at 80 ℃; for 2h;
87%
With potassium hydroxide; at 20 ℃; for 2h;
54%
With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 16h;
26%
With potassium hydroxide;
With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 48h;
With caesium carbonate; at 80 ℃;
With caesium carbonate; at 80 ℃; for 0.5h;
10.7 g
With caesium carbonate; at 80 ℃; for 0.5h;
With potassium carbonate; at 80 ℃; for 2h;
With caesium carbonate; at 80 ℃;
4-nitrophenoxyethyl tetrahydro-2H-pyran-2-yl ether
445283-41-0

4-nitrophenoxyethyl tetrahydro-2H-pyran-2-yl ether

2-(4-nitrophenoxy)ethanol
16365-27-8

2-(4-nitrophenoxy)ethanol

Conditions
Conditions Yield
With pyridinium p-toluenesulfonate; In methanol; at 23 ℃; for 16h;
100%
(2-chloroethoxy)trimethylsilane
18157-17-0

(2-chloroethoxy)trimethylsilane

2-(4-nitrophenoxy)ethanol
16365-27-8

2-(4-nitrophenoxy)ethanol

Conditions
Conditions Yield
With potassium carbonate; caesium carbonate; sodium iodide; In N,N-dimethyl-formamide; at 75 ℃; for 19.5h;
With sodium iodide; potassium carbonate; caesium carbonate; In N,N-dimethyl-formamide;
With sodium iodide; potassium carbonate; caesium carbonate; In N,N-dimethyl-formamide;
With sodium iodide; potassium carbonate; caesium carbonate; In N,N-dimethyl-formamide;
With sodium iodide; potassium carbonate; caesium carbonate; In N,N-dimethyl-formamide;
4-nitrophenol sodium salt
824-78-2

4-nitrophenol sodium salt

2-chloro-ethanol
107-07-3

2-chloro-ethanol

2-(4-nitrophenoxy)ethanol
16365-27-8

2-(4-nitrophenoxy)ethanol

Conditions
Conditions Yield
In DMF (N,N-dimethyl-formamide); at 100 ℃; for 72h;
92%
In N,N-dimethyl-formamide;
4-nitrophenoxyethyl selenocyanate

4-nitrophenoxyethyl selenocyanate

2-(4-nitrophenoxy)ethanol
16365-27-8

2-(4-nitrophenoxy)ethanol

Conditions
Conditions Yield
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 40 ℃; for 4h;
28%
[1,3]-dioxolan-2-one
96-49-1

[1,3]-dioxolan-2-one

2-(4-nitrophenoxy)ethanol
16365-27-8

2-(4-nitrophenoxy)ethanol

Conditions
Conditions Yield
With tetrabutyl ammonium fluoride; In N,N-dimethyl-formamide; at 170 ℃; for 21h; Inert atmosphere; Schlenk technique;
98%
With potassium carbonate; In N,N-dimethyl-formamide; at 110 ℃; for 16h; Inert atmosphere;
89%
With tetraethylammonium iodide; at 150 ℃;

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