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Usage

Uses

Used in Dye Industry:
4-Acetamidobenzenesulfinic Acid Sodium Salt is used as a key intermediate in the synthesis of cyanine dyes for the dye industry. These dyes are widely used in various applications, including biological imaging, solar cells, and other optical devices, due to their unique photophysical properties and high absorption coefficients.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 4-Acetamidobenzenesulfinic Acid Sodium Salt may also have potential applications in the pharmaceutical industry as a precursor for the synthesis of various pharmaceutical compounds. Its reactivity and functional groups can be utilized to create a range of therapeutic agents.
Used in Chemical Research:
4-Acetamidobenzenesulfinic Acid Sodium Salt can be used as a research compound in the field of organic chemistry. Its unique structure and properties make it a valuable tool for studying various chemical reactions and mechanisms, contributing to the advancement of chemical knowledge and the development of new synthetic methods.

Upstream product

• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 103-84-4 Acetanilid 
• 3660-40-0 S-phenyl 4-acetamidobenzenesulfonothioate 

Downstream Products

• 6305-64-2 4-(Butylsulfonyl)acetanilid 
• 78021-44-0 4-iodomethanesulfonyl-aniline 
• 100862-20-2 acetic acid-[4-(2-diethylamino-ethanesulfonyl)-anilide] 
• 6305-57-3 4-acetamidophenyl benzyl sulfone 
• 86810-69-7 N-[4-(propylsulfonyl)phenyl]acetamide 
• 88881-74-7 ethyl 2-((4-acetamidophenyl)sulfonyl)acetate 
• 130188-79-3 N-(4-((2-oxo-2-phenylethyl)sulfonyl)phenyl)acetamide 
• 408351-82-6 acetic acid-[4-(2-amino-5-dimethylamino-benzenesulfonyl)-anilide] 
• 52183-58-1 1,2-Di(4-acetamidophenylsulphono)ethane 
• 3729-42-8 N-(4-(allylsulfonyl)phenyl)acetamide 
• 4999-02-4 acetic acid-[4-(2-oxo-propane-1-sulfonyl)-anilide] 
• 130188-92-0 acetic acid-{4-[2-(4-bromo-phenyl)-2-oxo-ethanesulfonyl]-anilide} 
• 27375-52-6 acetic acid-[4-(2-hydroxy-ethanesulfonyl)-anilide] 
• 34764-83-5 4-(4-acetylamino-benzenesulfonylsulfanyl)-morpholine 

Relevant academic research and scientific papers

Aromatic sulfinic acid compound and preparation method thereof

The invention relates to a preparation method of an aromatic sulfinic acid compound, which comprises the following steps: dissolving an aromatic compound in a liquid coordination complex, and introducing sulfur dioxide to carry out Friedel-Crafts acylation reaction under the protection of inert gas to prepare the aromatic sulfinic acid compound. According to the preparation method, the liquid coordination complex prepared from the metal and the organic ligand is used as the catalyst and the solvent, other organic solvents do not need to be additionally added, the reaction rate is high, the yield is high, the product purity is high and can reach 97% on the whole, aftertreatment is simple, and the preparation method is suitable for large-scale production.

Unique para-aminobenzenesulfonyl oxadiazoles as novel structural potential membrane active antibacterial agents towards drug-resistant methicillin resistant Staphylococcus aureus

A class of structurally unique para-aminobenzenesulfonyl oxadiazoles as new potential antimicrobial agents was designed and synthesized from acetanilide. Some target para-aminobenzenesulfonyl oxadiazoles showed antibacterial potency. Noticeably, hexyl derivative 8b (MIC = 1 μg/mL) was more active than norfloxacin against drug resistant MRSA. Compound 8b was able to disturb the membrane effectively and intercalate into deoxyribonucleic acid (DNA) to form a steady 8b-DNA complex, which might be responsible for bacterial metabolic inactivation. Molecular docking indicated that 8b could interact with DNA topoisomerase IV through noncovalent interactions to form a supramolecular complex and hinder the function of this enzyme. These results indicated that hexyl derivative 8b deserved further investigation as a new lead compound.

Enhancing the Potential of Miniature-Scale DNA-Compatible Radical Reactions via an Electron Donor-Acceptor Complex and a Reversible Adsorption to Solid Support Strategy

DNA-encoded library (DEL) technology is a powerful tool in the discovery of bioactive probe molecules and drug leads. Mostly, the success in DEL technology stems from the molecular diversity of the chemical libraries. However, the construction of DELs has been restricted by the idiosyncratic needs and the required low concentration (～1 mM or less) of the library intermediate. Here, we report visible-light-promoted on-DNA radical coupling reactions via an electron donor-acceptor (EDA) complex and a reversible adsorption to solid support (RASS) strategy. This protocol provides a unique solution to the challenges of increasing the reactivity of highly diluted DNA substrates and reducing the residues of heavy metals from photocatalysts. A series of on-DNA indole sulfone and selenide derivatives were obtained with good to quantitative conversions. It is anticipated that these mild-condition on-DNA radical reactions will significantly improve the chemical diversity of DELs and find widespread utility to DEL construction.

Visible-light-driven electron donor-acceptor complex induced sulfonylation of diazonium salts with sulfinates

This work reports an efficient sulfonylation reaction enabled by a visible-light-induced radical coupling reaction between phenyl/heterocyclic diazonium salts and sulfinates. Mechanistic experiments disclosed the formation of a versatile electron donor-acceptor (EDA) complex. This transformation is characterized by an easy operational procedure under mild conditions which avoids transition metals, ligands, catalysts, and oxidants.

Metal-Free Chemoselective Reaction of Sulfoxonium Ylides and Thiosulfonates: Diverse Synthesis of 1,4-Diketones, Aryl Sulfursulfoxonium Ylides, and β-Keto Thiosulfones Derivatives

A diverse chemoselective insertion reaction of sulfoxonium ylides and thiosulfonates under transition-metal-free conditions is developed, which successfully affords 1,4-diketone compounds, arylthiosulfoxide-ylides, and β-keto thiosulfones, respectively. The nucleophilic addition of two molecular sulfoxonium ylides to construct sulfone-substituted 1,4-dione compounds is the highlight of this work.

Fe-based metal-organic frameworks for the synthesis of N-arylsulfonamides via the reactions of sodium arylsulfinates or arylsulfonyl chlorides with nitroarenes in water

A newly developed chemoselective reaction of sodium arylsulfinates or arylsulfonyl chlorides with nitroarenes has been disclosed. The chemistry, in which non-toxic water and recyclable iron-based metal-organic frameworks are employed as the solvent and catalyst, respectively, provides an efficient approach for the generation of N-arylsulfonamides, which are widely present in biologically active compounds and drugs, rendering this methodology attractive to both synthetic and medicinal chemistry.

Synthesis of arylstannanes by palladium-catalyzed desulfitative coupling reaction of sodium arylsulfinates with distannanes

A novel Pd-catalyzed desulfitative cross-coupling reaction of sodium arylsulfinates with hexaalkyl distannanes is realized, allowing the facile synthesis of functionalized arylstannanes with moderate to excellent yields. The successful implement of gram-scale synthesis and tandem Stille coupling reaction demonstrates the potential applications of this method in organic synthesis.

Convenient method for preparation of aryl sulfinates from arenes and DABSO as the SO2 surrogates

A safe and efficient protocol for the synthesis of aryl sulfinates from arenes and 1,4-diazabicyclo[2,2,2]octane bis(sulfur dioxide) (DABSO) under mild conditions is described. Through in situ infrared spectroscopic studies, a plausible mechanism for the sulfination reaction is proposed as well.

Design, synthesis and antimicrobial evaluation of novel benzimidazole-incorporated sulfonamide analogues

A novel series of benzimidazole-incorporated sulfonamide analogues were designed and synthesized with an effort to overcome the increasing antibiotic resistance. Compound 5c gave potent activities against Gram-positive bacteria and fungi, and 2,4-dichlorobenzyl derivative 5g showed good activities against Gram-negative bacteria. Both of these two active molecules 5c and 5g could effectively intercalate into calf thymus DNA to form compound?DNA complex respectively, which might block DNA replication to exert their powerful antimicrobial activity. Molecular docking experiments suggested that compounds 5c and 5g could insert into base-pairs of DNA hexamer duplex by the formation of hydrogen bonds with guanine of DNA. The transportation behavior of these highly active compounds by human serum albumin (HSA) demonstrated that the electrostatic interactions played major roles in the strong association of active compounds with HSA, and which was also confirmed by the full geometry calculation optimizations.

Preparation method of aromatic sulfinic acid compound

The invention relates to a preparation method of an aromatic sulfinic acid compound. The preparation method includes the steps of: with Lewis acid as a catalyst, performing a Friedel-Crafts acylation reaction to an aromatic compound as a raw material with 1,4-diazabicyclo[2.2.2]octane (DABSO) in a solvent to generate a corresponding aromatic sulfinic acid compound. Compared with industrial preparation methods for the aromatic sulfinic acid compound in the prior art, the method can synthesize the aromatic sulfinic acid compound in one step, so that experiment operations are simplified and a high-polluting chlorosulfonation step is avoided. The method has mild reaction conditions, wherein the reaction can be carried out under a common normal temperature condition, so that a large amount of energy consumption in production is reduced. The DABSO, compared with gas-phase SO2, is convenient to store and transport, has stable properties at normal temperature and under normal pressure and has safe and simple operations. The raw materials are low in cost and easy to obtain, thus reducing production cost. The method has huge potential in practical use.