7244-77-1

Usage

Uses

Used in Chemical Synthesis:
P-Propoxynitrobenzene is utilized as an intermediate in the synthesis of other organic compounds, playing a crucial role in the production of various chemical products.
Used in Organic Chemical Reactions:
It serves as a reagent in organic chemical reactions, facilitating specific transformations and processes in the field of organic chemistry.

InChI:InChI=1/C9H11NO3/c1-2-7-13-9-5-3-8(4-6-9)10(11)12/h3-6H,2,7H2,1H3

Upstream product

• 71-23-8 propan-1-ol 
• 100-17-4 para-methoxynitrobenzene 
• 1124-31-8 potassium 4-nitrophenolate 
• 106-94-5 propyl bromide 
• 350-46-9 4-Fluoronitrobenzene 
• 29843-53-6 dimethyl(p-nitrophenyl)sulfonium perchlorate 
• 100-02-7 4-nitro-phenol 
• 6819-41-6 sodium n-propoxide 
• 100-00-5 4-chlorobenzonitrile 
• 540-54-5 1-Chloropropane 
• 824-78-2 4-nitrophenol sodium salt 
• 1568-66-7 1-allyloxy-4-nitrobenzene 
• 100-29-8 1-ethoxy-4-nitrobenzene 
• 107-08-4 1-iodo-propane 

Downstream Products

• 4469-80-1 4-propoxyaniline 
• 90415-73-9 2-chloro-4-propoxyaniline 
• 2496-27-7 4-propoxy-4'-hydroxyazobenzene 

Relevant academic research and scientific papers

Inclusion complexes of a new family of non-ionic amphiphilic dendrocalix[4]arene and poorly water-soluble drugs naproxen and ibuprofen

The inclusion complexes of a new family of nonionic amphiphilic calix[4]arenes with the anti-inflammatory hydrophobic drugs naproxen (NAP) and ibuprofen (IBP) were investigated. The effects of the alkyl chain's length and the inner core of calix[4]arenes on the interaction of the two drugs with the calix[4]arenes were explored. The inclusion complexes of Amphiphiles 1a-c with NAP and IBP increased the solubility of these drugs in aqueous media. The interaction of 1a-c with the drugs in aqueous media was investigated through fluorescence, molecular modeling, and 1H-NMR analysis. TEM studies further supported the formation of inclusion complexes. The length of lipophilic alkyl chains and the intrinsic cyclic nature of cailx[4]arene derivatives 1a-c were found to have a significant impact on the solubility of NAP and IBP in pure water.

Properties of liquid crystals and Cu2+ recognition based on Schiff bases

Two series of new Schiff base compounds were synthesized. For Schiff base compounds with a pyridine nitrogen atom in 4-position (7a-e), their supramolecular hydrogen bonding complexes show good liquid crystal properties. However, no liquid crystal property is observed for 8a-e. Results of theoretical calculations demonstrate that it is the intermolecular hydrogen bond of Schiff base compounds (8a-e) that prevents the formation of supramolecular hydrogen bonding. The Schiff base compounds, with terminal alkoxy chains, can recognize Cu2+ selectively with a color change. Nevertheless, others cannot recognize Cu2+.

Chromogenic nitrophenolate-based substrates for light-driven hybrid P450 BM3 enzyme assay

The incorporation of a p-nitrophenoxy moiety in substrates has enabled the development of colorimetric assays to rapidly screen for O-demethylation activity of P450 enzymes. For the light-driven hybrid P450 BM3 enzymes, where a Ru(II) photosensitizer powers the enzyme upon visible light irradiation, we have investigated a family of p-nitrophenoxy derivatives as useful chromogenic substrates compatible with the light-driven approach. The validation of this assay and its adaptability to a 96-well plate format will enable the screening of the next generation of hybrid P450 BM3 enzymes towards C-H bond functionalization of non-natural substrates.

Dual thermo- and light-responsive nanorods from self-assembly of the 4-propoxyazobenzene-terminated poly(N-isopropylacrylamide) in aqueous solution

Abstract Both temperature and light stimuli-responsive 4-propoxyazobenzene-terminated poly(N-isopropylacrylamide)s (PNIPAMs) were successfully synthesized by the atom transfer radical polymerization (ATRP) of NIPAM. 1H NMR and UV-vis absorption spectra indicated rapid photoisomerization rate of 4-propoxyazobenzene moiety. Interestingly, the lower critical solution temperature (LCST) for PNIPAM aqueous solution clearly decreased after UV irradiation, and the repeated LCST difference (ΔTmaxy = 5°C) depended on both the number-average molecular weight and amount of azobenzene chromophore. Dynamic light scattering (DLS) and static light scattering (SLS) measurements showed that the PNIPAM aqueous solution could self-assemble into nano-micelles with 4-propoxyazobenzene as the hydrophobic cores and PNIPAM chains as the hydrophilic shells. UV irradiation induced the increase of particle size due to the formation of much looser cores of cis-azobenzene. TEM images showed the presence of both nanorods and spherical micelles. After UV irradiation, the unstable spherical micelles transformed to metastable nanorods, then to longer rods, and finally the longer rods began to transform to flake-like particles via horizontal inter-rod aggregation above LCST.

Enhanced Reactivity of Aerobic Diimide Olefin Hydrogenation with Arylboronic Compounds: An Efficient One-Pot Reduction/Oxidation Protocol

A catalyst-free and efficient method for simultaneous olefin hydrogenation and oxidation of arylboronate esters to phenols with hydrazine hydrate and molecular oxygen is presented. The process is based on the utilization of a readily available Lewis acidic arylboron compound, which evades common problems associated with the catalyst-free aerobic hydrogenation of olefins with diimide. Using an operationally simple procedure, the protocol smoothly delivers phenol derivatives and various alkanes in excellent yields with remarkable functional group compatibility. The method allows the reaction to be scaled up to 1 g of the starting materials.

Continuous flow reduction of artemisinic acid utilizing multi-injection strategies - Closing the gap towards a fully continuous synthesis of antimalarial drugs

One of the rare alternative reagents for the reduction of carbon-carbon double bonds is diimide (HN=NH), which can be generated in situ from hydrazine hydrate (N2H4·H2O) and O2. Although this selective method is extremely clean and powerful, it is rarely used, as the rate-determining oxidation of hydrazine in the absence of a catalyst is relatively slow using conventional batch protocols. A continuous high-temperature/high-pressure methodology dramatically enhances the initial oxidation step, at the same time allowing for a safe and scalable processing of the hazardous reaction mixture. Simple alkenes can be selectively reduced within 10-20 min at 100-120°C and 20 bar O2 pressure. The development of a multi-injection reactor platform for the periodic addition of N2H4·H2O enables the reduction of less reactive olefins even at lower reaction temperatures. This concept was utilized for the highly selective reduction of artemisinic acid to dihydroartemisinic acid, the precursor molecule for the semisynthesis of the antimalarial drug artemisinin. The industrially relevant reduction was achieved by using four consecutive liquid feeds (of N2H4·H2O) and residence time units resulting in a highly selective reduction within approximately 40 min at 60°C and 20 bar O2 pressure, providing dihydroartemisinic acid in ≥93% yield and ≥95% selectivity.

An insight into the extraction of transition metal ions by picolinamides associated with intramolecular hydrogen bonding and rotational isomerization

The clear connection between molecular structures of N-substituted picolinamides and extraction behaviour has been rationalized by highlighting the relationship between intramolecular hydrogen bonding and rotational isomerism. To this aim aromatic pyridine-2,6-dicarboxamides 1a-1c with N-substitution and their analogues 3a and 3b containing intramolecular hydrogen bonds were designed and synthesized. The results from the liquid-liquid extraction towards some representative transition metal picrates including Ag+, Hg 2+, Pb2+, Cd2+, Zn2+, Cu 2+, Co2+ and Ni2+ salts demonstrated that the higher selectivity and efficiency towards Hg2+ (88.6-95.4%) over other metal cations stem mainly from N-substitution via disruption of intramolecular H-bonding. X-ray structural analysis, and ordinary and variable-temperature proton and carbon NMR experiments provided supporting information for expounding the difference in extraction ability among these ligands, particularly the importance of N-substitution that leads to the formation of rotamers affecting the extraction process.

In situ generation of diimide from hydrazine and oxygen: Continuous-flow transfer hydrogenation of olefins

No catalyst required! A highly efficient, catalyst-free process to generate diimide in situ from hydrazine monohydrate and molecular oxygen for the selective reduction of alkenes has been developed. The use of a gas-liquid segmented flow system allowed safe operating conditions and dramatically enhanced this atom-economical reaction, resulting in short processing times. Copyright

Magnetically recoverable catalytic Co-Co2B nanocomposites for the chemoselective reduction of aromatic nitro compounds

Magnetically recoverable and recyclable Co-Co2B nanocomposites are described for the catalytic and chemoselective reduction of nitroarenes using two different hydrogen sources, sodium borohydride and hydrazine hydrate. Both the systems display an interesting chemoselective reduction switch. The kinetics of reduction of nitroaromatics were studied for the first time and follow nitroreductase enzyme-like kinetics with exceedingly high Kcat (5.2 × 104 s-1) and Kcat/KM (4.4 × 106 M-1 s-1) values, reaching the state of catalytic perfection. The recyclability of the catalyst system was studied by magnetically recovering the nano composite catalyst.

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.