61827-67-6

Usage

Uses

Used in Chemical Synthesis:
4-ACETYLBENZENESULFONIC ACID SODIUM SALT is used as a key intermediate in the synthesis of various organic compounds, particularly those with potential applications in the pharmaceutical and chemical industries. Its unique structure allows for further functionalization and modification, making it a versatile building block for the development of new molecules.
Used in Imaging and Detection:
4-ACETYLBENZENESULFONIC ACID SODIUM SALT is used as a precursor for the preparation of Near-Infrared (NIR) to Short-Wavelength Infrared (SWIR) fluorescent compounds. These compounds are valuable for imaging and detection purposes, as they can be used to enhance the visualization of specific targets or markers in various applications, such as medical diagnostics, environmental monitoring, and security.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-ACETYLBENZENESULFONIC ACID SODIUM SALT is used as a starting material for the synthesis of various drug candidates. Its unique chemical properties make it an attractive candidate for the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
4-ACETYLBENZENESULFONIC ACID SODIUM SALT is also used in academic and industrial research settings, where it serves as a valuable tool for studying the properties and reactivity of various chemical systems. Its unique structure and functional groups make it an interesting subject for exploration in the field of organic chemistry.

InChI:InChI=1/C8H8O4S/c1-6(9)7-2-4-8(5-3-7)13(10,11)12/h2-5H,1H3,(H,10,11,12)/p-1

Upstream product

• 14995-38-1 ethylbenzene-4-sulphonic acid sodium salt 
• 2695-37-6 sodium 4-styrenesulfonate 

Downstream Products

• 97326-86-8 C₂₃H₁₆O₈S₂ 
• 92237-62-2 disodium salt of 2-(4-methoxy-3-sulphophenyl)vinyl 4-sulphophenyl ketone 
• 151460-16-1 2,4-diphenyl-6-(4-sulfophenyl)pyrylium 
• 106-51-4 p-benzoquinone 
• 99-93-4 4-Hydroxyacetophenone 
• 197240-09-8 4-[3-(4-fluorophenyl)-2,3-dihydro-2-oxo-4-oxazolyl]benzenesulfonamide 
• 259227-06-0 4-acetyl-N,N-dibenzylbenzenesulfonamide 

Relevant academic research and scientific papers

Precursor transformation during molecular oxidation catalysis with organometallic iridium complexes

We present evidence for Cp* being a sacrificial placeholder ligand in the [Cp*IrIII(chelate)X] series of homogeneous oxidation catalysts. UV-vis and 1H NMR profiles as well as MALDI-MS data show a rapid and irreversible loss of the Cp* ligand under reaction conditions, which likely proceeds through an intramolecular inner-sphere oxidation pathway reminiscent of the reductive in situ elimination of diolefin placeholder ligands in hydrogenation catalysis by [(diene)MI(L,L′)]+ (M = Rh and Ir) precursors. When oxidatively stable chelate ligands are bound to the iridium in addition to the Cp*, the oxidized precursors yield homogeneous solutions with a characteristic blue color that remain active in both water- and CH-oxidation catalysis without further induction period. Electrophoresis suggests the presence of well-defined Ir-cations, and TEM-EDX, XPS, 17O NMR, and resonance-Raman spectroscopy data are most consistent with the molecular identity of the blue species to be a bis-μ-oxo di-iridium(IV) coordination compound with two waters and one chelate ligand bound to each metal. DFT calculations give insight into the electronic structure of this catalyst resting state, and time-dependent simulations agree with the assignments of the experimental spectroscopic data. [(cod)Ir I(chelate)] precursors bearing the same chelate ligands are shown to be equally effective precatalysts for both water- and CH-oxidations using NaIO4 as chemical oxidant.

Mechanism of ketone and alcohol formations from alkenes and alkynes on the head-to-head 2-pyridonato-bridged cis-diammineplatinum(III) dinuclear complex

Reactions of the head-to-head 2-pyridonato-bridged cis-diammineplatinum(III) dinuclear complex having nonequivalent two platinum atoms, Pt(N2O2) and Pt(N4), with p-styrenesulfonate, 2-methyl-2-propene-1-sulfonate, 4-penten-1-ol, and 4-pentyn-ol were studied kinetically. Under the pseudo first-order reaction conditions that the concentration of the PtIII dinuclear complex is much smaller than that of olefin, a consecutive basically four-step reaction was observed: the olefin π-coordinates preferentially to the Pt(N2O2) in the first step (step 1), followed by the second π-coordination of another olefin molecule to the Pt(N4) (step 2). In the next step (step 3), the nucleophilic attack of water to the coordinated olefin triggers the π-σ bond conversion on the Pt(N2O2), and the second π-bonding olefin molecule on the Pt(N4) is released. Finally, reductive elimination occurs to the alkyl group on the Pt(N2O2) to produce the alkyl compound (step 4). The first water substitution with olefin (step 1) occurs to the diaqua and aquahydroxo forms of the complex, whereas the second substitution (step 2) proceeds either on the coordinated OH-on the Pt(N4) (path a) or on the coordinatively unsaturated five-coordinate intermediate of the Pt(N4) (path b), in addition to the common substitution of H2O (path c). The reactions of p-styrenesulfonate and 2-methyl-2-propene-1-sulfonate proceed through paths b and c, whereas the reactions of 4-penten-1-ol and 4-pentyn-1-ol proceed through paths a and c. This difference reflects the difference of the trans effect and/or trans influence of the π-coordinated olefins on the Pt(N2O2). The pentacoordinate state in path b is employed only by the sulfo-olefins, because these exert stronger trans effect. The steps 3 and 4 reflect the effect of the axial alkyl ligand (R) on the charge localization R-PtIV(N2O2)-PtII (N4))and delocalization (R-PtIII(N2O2)-PtIII (N4)(N4)-OH2); when R is p-styrenesulfonate having an electron withdrawing group, the charge localization in the dimer is less pronounced and the water molecule on the Pt(N4) atom is retained (RPtIII(N2O2)-PtIII (N4)-OH2) in the intermediate state. In both routes, the alkyl group undergoes nucleophilic attack of water, and the oxidized products are released via reductive elimination.

A cobalt-substituted Keggin-Type polyoxometalate for catalysis of oxidative aromatic cracking reactions in water

Efficient detoxification of harmful benzene rings into useful carboxylic acids in water is indispensable for achieving a clean water environment. We report herein that oxidative aromatic cracking (OAC) reactions in water were achieved using a catalytic system with a cobalt-substituted Keggin-Type polyoxometalate (Co-POM) as a catalyst, an Oxone monopersulfate compound as a sacrificial oxidant and sodium bicarbonate as an additive under mild conditions. Sodium bicarbonate plays a crucial role in the selective OAC reactions by Co-POM using ethylbenzenesulfonate as a model substrate. The reactive species was characterized to be a cobalt(iii)-oxyl species based on 31P NMR, UV-vis spectroscopic, kinetic, and theoretical analyses. The electrophilicity of the cobalt(iii)-oxyl species was demonstrated by a linear relationship with a negative slope in the Hammett plots of initial rates obtained from the OAC reactions of m-xylenesulfonate derivatives. Besides, we have verified the degradation pathway of the OAC reactions using benzene as a model substrate in the catalytic system. The degradation was initiated by an electrophilic attack of the cobalt(iii)-oxyl species on benzene to yield phenol followed by producing catechol, muconic acid, maleic/fumaric acid, tartaric acid derivatives and formic acid on the basis of 1H NMR spectroscopic analysis.

Cp? versus Bis-carbonyl iridium precursors as CH oxidation precatalysts

We previously reported a dimeric IrIV-oxo species as the active water oxidation catalyst formed from a Cp?Ir(pyalc)Cl {pyalc = 2-(2′-pyridyl)-2-propanoate} precursor, where the Cp? is lost to oxidative degradation during catalyst activation; this system can also oxidize unactivated CH bonds. We now show that the same Cp?Ir(pyalc)Cl precursor leads to two distinct active catalysts for CH oxidation. In the presence of external CH substrate, the Cp? remains ligated to the Ir center during catalysis; the active species-likely a highvalent Cp?Ir(pyalc) species-will oxidize the substrate instead of its own Cp?. If there is no external CH substrate in the reaction mixture, the Cp? will be oxidized and lost, and the active species is then an iridium-μ-oxo dimer. Additionally, the recently reported Ir(CO)2(pyalc) water oxidation precatalyst is now found to be an efficient, stereoretentive CH oxidation precursor. We compare the reactivity of Ir(CO)2(pyalc) and Cp?Ir(pyalc)Cl precursors and show that both can lose their placeholder ligands, CO or Cp?, to form substantially similar dimeric IrIV-oxo catalyst resting states. The more efficient activation of the bis-carbonyl precursor makes it less inhibited by obligatory byproducts formed from Cp? degradation, and therefore the dicarbonyl is our preferred precatalyst for oxidation catalysis.

METAL OXIDE-ORGANIC HYBRID MATERIALS FOR HETEROGENEOUS CATALYSIS AND METHODS OF MAKING AND USING THEREOF

Catalysts prepared from abundant, cost effective metals, such as cobalt, nickel, chromium, manganese, iron, and copper, and containing one or more neutrally charged ligands (e.g., monodentate, bidentate, and/or polydentate ligands) and methods of making and using thereof are described herein. Exemplary ligands include, but are not limited to, phosphine ligands, nitrogen-based ligands, sulfur-based ligands, and/or arsenic-based ligands. In some embodiments, the catalyst is a cobalt-based catalyst or a nickel-based catalyst. The catalysts described herein are stable and active at neutral pH and in a wide range of buffers that are both weak and strong proton acceptors. While its activity is slightly lower than state of the art cobalt-based water oxidation catalysts under some conditions, it is capable of sustaining electrolysis at high applied potentials without a significant degradation in catalytic current. This enhanced robustness gives it an advantage in industrial and large-scale water electrolysis schemes.

IRIDIUM COMPLEXES FOR ELECTROCATALYSIS

Solution-phase (e.g., homogeneous) or surface-immobilized (e.g., heterogeneous) electrode-driven oxidation catalysts based on iridium coordination compounds which self-assemble upon chemical or electrochemical oxidation of suitable precursors and methods of making and using thereof are. Iridium species such as {[Ir(LX)x(H2O)y(μ-O)]zm+}n wherein x, y, m are integers from 0-4, z and n from 1-4 and LX is an oxidation-resistant chelate ligand or ligands, such as such as 2(2-pyridyl)-2-propanolate, form upon oxidation of various molecular iridium complexes, for instance [Cp*Ir(LX)OH] or [(cod)Ir(LX)] (Cp*=pentamethylcyclopentadienyl, cod=cis-cis,1,5-cyclooctadiene) when exposed to oxidative conditions, such as sodium periodate (NaIO4) in aqueous solution at ambient conditions.

Co(ii), a catalyst for selective conversion of phenyl rings to carboxylic acid groups

An inexpensive protocol for the conversion of -C6H4R into -COOH groups using Co(ii)-Oxone mixture as the catalytic system is described. A series of substrates containing substituted and non-substituted phenyl groups could be selectively converted into carboxylic acids. Initial mechanistic data have been provided.

Cp* iridium precatalysts for selective C-h oxidation with sodium periodate as the terminal oxidant

Sodium periodate (NaIO4) is shown to be a milder and more efficient terminal oxidant for C-H oxidation with CpIr (Cp* = C 5Me5) precatalysts than ceric(IV) ammonium nitrate. Synthetically useful yields, regioselectivities, and functional group tolerance were found for methylene oxidation of substrates bearing a phenyl, ketone, ester, or sulfonate group. Oxidation of the natural products (-)-ambroxide and sclareolide proceeded selectively, and retention of configuration was seen in cis-decalin hydroxylation. At 60 C, even primary C-H bonds can be activated: whereas methane was overoxidized to CO2 in 39% yield without giving partially oxidized products, ethane was transformed into acetic acid in 25% yield based on total NaIO4. 18O labeling was demonstrated in cis-decalin hydroxylation with 18OH2 and NaIO 4. A kinetic isotope effect of 3.0 ± 0.1 was found in cyclohexane oxidation at 23 C, suggesting C-H bond cleavage as the rate-limiting step. Competition experiments between C-H and water oxidation show that C-H oxidation of sodium 4-ethylbenzene sulfonate is favored by 4 orders of magnitude. In operando time-resolved dynamic light scattering and kinetic analysis exclude the involvement of metal oxide nanoparticles and support our previously suggested homogeneous pathway.

A low-spin ruthenium(IV)-oxo complex: Does the spin state have an impact on the reactivity?

Spin doesn't matter: A ruthenium(II)-aqua complex bearing a pentadentate pyridylamine with a carboxylate group as a ligand affords a seven-coordinate low-spin (S=0) ruthenium(IV)-oxo complex (see structure) by oxidation through proton-coupled electron transfer. Comparison of the reactivity of the low-spin and an intermediate-spin (S=1) RuIV-oxo complexes revealed that the spin state does not affect the reactivity of catalytic oxidation of organic compounds.

Degradation of sodium 4-dodecylbenzenesulphonate photoinduced by Fe(III) in aqueous solution

The Fe(III)-photoinduced degradation of 4-dodecylbenzenesulphonate (DBS) in aqueous solution was investigated. The mixing of DBS (1 mm) and Fe(III) (1 mm) solutions immediately led to the formation of a precipitate that contained DBS and monomeric Fe(OH)2+, the predominant Fe(III) species. Both species were also present in the supernatant. Irradiation of the supernatant solution resulted in a photoredox process that yielded Fe(II) and ·OH radicals. The disappearance of DBS was shown to involve only attack by ·OH radicals; the quantum yield of DBS disappearance is similar to the quantum yield of ·OH radical formation. A wavelength effect was also observed; the rate of DBS disappearance was higher for shorter wavelength irradiation. Five photoproducts, all containing the benzene sulphonate group, were identified. ·OH radicals preferentially abstract hydrogen from the carbon in the α position of the aromatic ring. The results show that the Fe(III)-photoinduced degradation of DBS could be used as an alternative method for polluted water treatment. (C) 2000 Elsevier Science Ltd.