1124-31-8

Usage

Uses

Used in Organic Synthesis:
Phenol, 4-nitro-, potassium salt (1:1) is used as a reagent in organic synthesis for its ability to donate electrons and participate in various chemical reactions, facilitating the formation of new compounds and structures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Phenol, 4-nitro-, potassium salt (1:1) is utilized as an intermediate in the synthesis of certain drugs, contributing to the development of new medicinal compounds.
Used in Dye and Pigment Production:
Phenol, 4-nitro-, potassium salt (1:1) is employed in the production of dyes and pigments, where its chemical properties are leveraged to create a range of colorants for various applications.
Used in Chemical Product Manufacturing:
Phenol, 4-nitro-,potassium salt (1:1) also finds use in the manufacturing of other chemical products, where its unique characteristics are harnessed to produce a variety of materials and substances.
Safety Note:
Due to its potential toxicity and hazardous properties, Phenol, 4-nitro-, potassium salt (1:1) should be handled with care, adhering to proper safety protocols and guidelines to minimize risks.

Upstream product

• 31898-87-0 4-(4-nitro-phenoxy)-azetidin-2-one 
• 81408-98-2 p-nitrophenyl acetate-d3 
• 127-08-2 potassium acetate 
• 1941-22-6 CD₃COO^(1-)*K⁽¹⁺⁾=CD₃COOK 
• 108-43-0 3-monochlorophenol 
• 17175-16-5 p-nitrophenyl methyl carbonate 
• 28177-48-2 2,6-difluorophenol 
• 150-76-5 4-methoxy-phenol 
• 108-95-2 phenol 
• 917-58-8 potassium ethoxide 
• 311-45-5 paraoxon 
• 56-38-2 parathion 
• 100-17-4 para-methoxynitrobenzene 
• 100-02-7 4-nitro-phenol 

Downstream Products

• 28355-48-8 2-(3-nitrophenoxy)pyridine 
• 55502-03-9 1-(4-bromobutoxy)-4-nitrobenzene 
• 14467-68-6 1-nitro-4-(4-(4-nitrophenoxy)butoxy)benzene 
• 7244-78-2 1-butoxy-4-nitrobenzene 
• 35293-09-5 1,4-bis((4-nitrophenoxy)methyl)benzene 
• 17357-66-3 furan-2-carboxylic acid-(2-nitro-phenyl ester) 
• 850852-87-8 4-methyl-5-(4-nitro-phenoxy)-thiazol-2-ylamine 
• 790704-35-7 3-nitro-2-(2-nitro-phenoxy)-pyridine 
• 229620-56-8 2-(4-nitrophenoxy)-3-nitropyridine 
• 4783-83-9 4-nitrophenyl-4-pyridyl ether 
• 33109-59-0 glutaric acid bis-(4-nitro-phenyl ester) 
• 98395-61-0 N-(2-(4-nitrophenoxy)ethyl)phthalimide 
• 101732-28-9 2-[4-(4-Nitrophenoxy)butyl]-1H-isoindole-1,3(2H)-dione 
• 115604-75-6 tetrakis[(4-nitrophenoxy)methyl]methane 

Relevant academic research and scientific papers

Identification of products in the reaction of 2-[(hydroxyimino)methyl]-1,3-dimethylimidazolium iodide with diethyl 4-nitrophenyl phosphate in alkaline medium

Products of the reaction of 2-[(hydroxyimino)methyl]-1,3-dimethylimidazolium iodide with diethyl 4-nitrophenyl phosphate in alkaline medium have been identified by electronic spectroscopy, one-(1H, 31P, 13C) and two-dimensional (1H-1H COSY, 1H-31P HMBC) NMR techniques, and NMR titration. 2-[(Hydroxyimino)-methyl]-1,3-dimethylimidazolium iodide has been found to act as nucleophile which is likely to be converted into 2-cyano-1,3-dimethylimidazolium. The other products are 4-nitrophenol and diethyl hydrogen phosphate. Other reaction paths, such as nucleophilic catalysis of the hydrolysis of diethyl 4-nitrophenyl phosphate by 2-[(hydroxyimino)methyl]-1,3-dimethylimidazolium iodide and formation of a stable phosphorylated product, have been ruled out.

TRANSITION STATES OF SOME ACYL TRANSFER REACTIONS IN ACETONITRILE

β-Deuterium isotope effect (β-DIE) studies of acyl transfer from aryl acetates to acetate ion in acetonitrile indicate the degree of tetrahedral character at the transition state (TS) to be small, and the same as in protic solvents.

Significant and differential acceleration of dephosphorylation of the insecticides, paraoxon and parathion, caused by alkali metal ethoxides.

In the reaction of paraoxon with alkali metal ethoxides, ion-paired EtO-M+ species are more reactive than the dissociated EtO- with the reactivity order EtO-Li+ EtO-Na+ > EtO-K+ > EtO-, while in the reaction of parathion, the reactivity follows the order

Alkali metal ion catalysis in nucleophilic displacement by ethoxide ion on p-nitrophenyl phenylphosphonate: Evidence for multiple metal ion catalysis1

In continuation of our studies of alkali metal ion catalysis and inhibition at carbon, phosphorus, and sulfur centers, the role of alkali metal ions in nucleophilic displacement reactions of p-nitrophenyl phenylphosphonate (PNPP) has been examined. All al

Catalytic nanoreactors for ester hydrolysis

Hydrolysis of 4-nitrophenyl benzoate (PNPB) in the presence of ionene nanoreactors was studied comparing the ionenes, poly[(dimethyl)-2-hydroxy propanodiyl chloride] (2-OH-33R1), poly[(methylbutyliminium)-2-hydroxy propanodiyl chloride] (2-OH-33R4) and poly[(methyloctyliminium)-2-hydroxy propanodiyl chloride] (2-OH-33R8). Methyl orange incorporation and study of viscosity showed that increase of the side chain length of the ionene enhances the ability to form globular hydrophobic microdomains. Catalytic hydrolysis of PNPB follows the order 2-OH-33R8 2-OH-33R4 > 2-OH-33R1, and 2-OH-33R8 has the lowest pKa that may reflect its higher hydrophobicity, which apparently influences the ionene nanoreactor reactivity. A lower pKa indicates easier deprotonation of the alkoxide group, which participates more effectively in the reaction and the 2-OH-33R8 functionalized ionene acts as a specially effective catalytic homogeneous nanoreactor.

Lewis Acidity Scale of Diaryliodonium Ions toward Oxygen, Nitrogen, and Halogen Lewis Bases

Equilibrium constants for the associations of 17 diaryliodonium salts Ar2I+X- with 11 different Lewis bases (halide ions, carboxylates, p-nitrophenolate, amines, and tris(p-anisyl)phosphine) have been investigated by titrations followed by photometric or conductometric methods as well as by isothermal titration calorimetry (ITC) in acetonitrile at 20 °C. The resulting set of equilibrium constants KI covers 6 orders of magnitude and can be expressed by the linear free-energy relationship lg KI = sI LAI + LBI, which characterizes iodonium ions by the Lewis acidity parameter LAI, as well as the iodonium-specific affinities of Lewis bases by the Lewis basicity parameter LBI and the susceptibility sI. Least squares minimization with the definition LAI = 0 for Ph2I+ and sI = 1.00 for the benzoate ion provides Lewis acidities LAI for 17 iodonium ions and Lewis basicities LBI and sI for 10 Lewis bases. The lack of a general correlation between the Lewis basicities LBI (with respect to Ar2I+) and LB (with respect to Ar2CH+) indicates that different factors control the thermodynamics of Lewis adduct formation for iodonium ions and carbenium ions. Analysis of temperature-dependent equilibrium measurements as well as ITC experiments reveal a large entropic contribution to the observed Gibbs reaction energies for the Lewis adduct formations from iodonium ions and Lewis bases originating from solvation effects. The kinetics of the benzoate transfer from the bis(4-dimethylamino)-substituted benzhydryl benzoate Ar2CH-OBz to the phenyl(perfluorophenyl)iodonium ion was found to follow a first-order rate law. The first-order rate constant kobs was not affected by the concentration of Ph(C6F5)I+ indicating that the benzoate release from Ar2CH-OBz proceeds via an unassisted SN1-type mechanism followed by interception of the released benzoate ions by Ph(C6F5)I+ ions.

Ambident Reactivity of Phenolate Anions Revisited: A Quantitative Approach to Phenolate Reactivities

Prompted by the observation that the regioselectivities of phenolate reactions (C versus O attack) are opposite to the predictions by the principle of hard and soft acids and bases, we performed a comprehensive experimental and computational investigation of phenolate reactivities. Rate and equilibrium constants for the reactions of various phenolate ions with benzhydrylium ions (Aryl2CH+) and structurally related quinone methides have been determined photometrically in polar aprotic solvents. Quantum chemical calculations at the SMD(MeCN)/M06-2X/6-31+G(d,p) level confirmed that O attack is generally favored under kinetically controlled conditions, whereas C attack is favored under thermodynamically controlled conditions. Exceptions are diffusion-limited reactions with strong electrophiles, which give mixtures of products arising from O and C attack, as well as reactions with metal alkoxides in nonpolar solvents, where oxygen attack is blocked by strong ion pairing. The Lewis basicity (LB) and nucleophilicity (N, sN) parameters of phenolates determined in this work can be used to predict whether their reactions with electrophiles are kinetically or thermodynamically controlled and whether the rates are activation- or diffusion-limited. Comparison of the measured rate constants for the reactions of phenolates with carbocations with the Gibbs energies for single-electron transfer manifests that these reactions proceed via polar mechanisms.

Impact of aryloxy initiators on the living and immortal polymerization of lactide

This report describes two different methodologies for the synthesis of aryl end-functionalized poly(lactide)s (PLAs) catalyzed by indium complexes. In the first method, a series of para-functionalized phenoxy-bridged dinuclear indium complexes [(NNO)InCl]2(μ-Cl)(μ-OPhR) (R = OMe (1), Me (2), H (3), Br (4), NO2 (5)) were synthesized and fully characterized. The solution and solid state structures of these complexes reflect the electronic differences between these initiators. The polymerization rates correlate with the electron donating ability of the phenoxy initiators: the para-nitro substituted complex 5 is essentially inactive. However, the para-methoxy variant, while less active than the ethoxy-bridged complex [(NNO)InCl]2(μ-Cl)(μ-OEt) (A), shows sufficient activity. Alternatively, aryl-capped PLAs were synthesized via immortal polymerization of PLA with A in the presence of a range of arylated chain transfer agents. Certain aromatic diols shut down polymerization by chelating one indium centre to form a stable metal complex. Immortal ROP was successful when using phenol, and 1,5-naphthalenediol. These polymers were analysed and chain end fidelity was confirmed using 1H NMR spectroscopy, MALDI-TOF mass spectrometry, and UV-Vis spectroscopy. This study shed light on possible speciation when attempting to generate PLA-lignin copolymers.

Tuning the intramolecular charge transfer (ICT) process in push-pull systems: Effect of nitro groups

The intramolecular charge transfer (ICT) process in donor-acceptor systems has tremendous importance in various physical and biological systems. Three nitrophenolate salts were synthesized and studied here. The ICT and π → π? transition processes were identified in these derivatives using UV-Vis spectroscopy and theoretical calculations. It was observed that by simple substitution with nitro groups, one can generate and control the ICT process by regulating the charge distribution over the molecule. While for a monosubstitute nitro derivative, only one ICT band was observed, additional ICT processes can be generated at will by introducing a second nitro group. The intensity of this second ICT channel can be regulated with introduction of a third nitro group. Further, the association constants and solvation processes for these potassium nitrophenolate derivatives were found to be drastically dependent on the number of ICT channels present in the molecule. Theoretical studies (MEP analysis) support the experimental observations presented here. The results show that by simply introducing additional acceptor groups to the system, one can tune the ICT band efficiently in a conjugate system.

Enthalpy-entropy correlations in reactions of aryl benzoates with potassium aryloxides in dimethylformamide

Temperature dependences of the relative reactivity of potassium aryloxides XC6H4O-K+ toward 4-nitrophenyl (1), 3-nitrophenyl (2), 4-chlorophenyl (3), and phenyl (4) benzoates in dimethylformamide (DMF) were studied using the competitive reactions technique. The rate constants kX for the reactions of 1 with potassium 4-cyanophenoxide, 2 with potassium 3-bromophenoxide, 3 with potassium 3-bromo-, 4-bromo-, and unsubstituted phenoxides, 4 with potassium 4-methoxy- and 3-methylphenoxides were measured at 25°C. Correlation analysis of the relative rate constants kX/kH(3-Me) and differences in the activation parameters (δδH≠and δ δS ≠) of competitive reactions revealed the existence of six isokinetic series. We investigated the substituent effect of X on the activation parameters for each isokinetic series and concluded that the reactions of aryl benzoates PhCO2C6H4Y with potassium aryloxides in DMF proceed via a four-step mechanism. The large ρ0(Y) and ρXY values at 25°C obtained for the reactions of 1-3 with potassium aryloxides with an electron-donating substituent refer to the rate-determining formation of the spiro-σ-complex. The Hammett plots for the reactions of 1 and 2 exhibit a downward curvature, causing the motion of the transition state for the rate-determining step according to a Hammond effect as the substituent in aryloxide changes from electron-donating to electron-withdrawing. Analysis of data in the terms of two-dimensional reaction coordinate diagrams leads to the conclusion that significant anti-Hammond effects arise in the cases of ortho-substituted and unsubstituted substrates. It was shown that the isokinetic and compensation effects observed for the reactions of aryl benzoates with potassium aryloxides in DMF can be interpreted in the terms of the electrostatic bonding between the reaction centers.