4533-95-3

Usage

Uses

Used in Organic Synthesis:
2-Chloro-5-nitro-benzenesulfonyl chloride is used as a synthetic building block for the creation of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, making it a valuable reagent in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Chloro-5-nitro-benzenesulfonyl chloride is used as an intermediate in the synthesis of various drug molecules. Its presence in the molecular structure can contribute to the desired biological activity of the final product, making it an essential component in the development of new medications.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, 2-Chloro-5-nitro-benzenesulfonyl chloride is utilized as a key intermediate in the synthesis of pesticides and other crop protection agents. Its chemical properties enable the development of compounds with improved efficacy and selectivity, contributing to more effective and environmentally friendly agricultural practices.
Used in Chemical Research:
2-Chloro-5-nitro-benzenesulfonyl chloride is also employed in academic and industrial research settings as a versatile reagent for exploring new chemical reactions and developing innovative synthetic methodologies. Its unique properties make it an attractive candidate for studying various aspects of organic chemistry, including reaction mechanisms, stereochemistry, and catalyst development.

InChI:InChI=1/C6H3Cl2NO4S/c7-5-2-1-4(9(10)11)3-6(5)14(8,12)13/h1-3H

Upstream product

• 6283-25-6 H₂NC₆H₃(Cl)NO₂ 
• 96-73-1 2-chloro-5-nitro-benzenesulfonic acid 
• 7790-94-5 chlorosulfonic acid 
• 100-00-5 4-chlorobenzonitrile 
• 946-30-5 2-chloro-5-nitrobenzenesulphonic acid sodium salt 

Downstream Products

• 109099-19-6 2-chloro-5-nitro-benzenesulfonic acid p-anisidide 
• 116-34-7 2-amino-5-nitro-benzenesulfonic acid-(N-ethyl-anilide) 
• 105837-49-8 2-chloro-5-nitro-benzenesulfonic acid anilide 
• 132318-00-4 2-chloro-5-nitro-benzenesulfonic acid-[2]naphthylamide 
• 104094-47-5 4-chloro-1-nitro-3-phenylsulfonylbenzene 
• 43001-63-4 2-chloro-5-nitro-benzenesulfonic acid phenyl ester 
• 96-72-0 2-chloro-5-nitrobenzenesulfonamide 
• 20201-05-2 4-chloro-3-((5-amino-2-chlorophenyl)disulfanyl)aniline 
• 61886-18-8 2-chloro-5-nitrobenzene sulfinic acid 
• 115561-03-0 1-fluoro-2-fluorosulfonyl-4-nitrobenzene 
• 173908-22-0 1-(2-Chloro-5-nitro-benzenesulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester 
• 173908-23-1 1-(2-Chloro-5-nitro-benzenesulfonyl)-1H-pyrrole-2-carboxylic acid ethyl ester 
• 899790-36-4 2-(3-methylphenoxy)-5-nitrobenzenesulfonamide 

Relevant academic research and scientific papers

Novel brilliant blue dye intermediate, reactive brilliant blue dye as well as preparation method and application of reactive brilliant blue dye

The invention discloses a novel brilliant blue dye intermediate, a reactive brilliant blue dye as well as a preparation method and application of thereactive brilliant blue dye, and relates to the field of reactive dyes. The preparation method of the reactive brilliant blue dye comprises the steps of a, Ullmann condensation, b, esterification and c, condensation. The reactive brilliant blue dye product prepared by the invention is high in solubility, strong in reactivity and high in fixation rate, is suitable for dip dyeing, pad dyeing and cold batch dyeing, and can reduce environmental pollution.

Design, Synthesis,In VitroandIn VivoCharacterization of Selective NKCC1 Inhibitors for the Treatment of Core Symptoms in down Syndrome

Intracellular chloride concentration [Cl-]iis defective in several neurological disorders. In neurons, [Cl-]iis mainly regulated by the action of the Na+-K+-Cl-importer NKCC1 and the K+-Cl-exporter KCC2. Recently, we have reported the discovery of ARN23746 as the lead candidate of a novel class of selective inhibitors of NKCC1. Importantly, ARN23746 is able to rescue core symptoms of Down syndrome (DS) and autism in mouse models. Here, we describe the discovery and extensive characterization of this chemical class of selective NKCC1 inhibitors, with focus on ARN23746 and other promising derivatives. In particular, we present compound 40 ( ARN24092 ) as a backup/follow-up lead within vivoefficacy in a mouse model of DS. These results further strengthen the potential of this new class of compounds for the treatment of core symptoms of brain disorders characterized by the defective NKCC1/KCC2 expression ratio.

Controllable Soil Degradation Rate of 5-Substituted Sulfonylurea Herbicides as Novel AHAS Inhibitors

Chlorsulfuron has been applied in wheat fields as a recognized herbicide worldwide, yet it was officially banned in China since 2014 for its soil persistence problem. On the basis of our previous research that 5-dimethylamino distinctively accelerated degradation rate in soils, a modified amino moiety (Ia-c) and monosubstituted amino group (Id-e) were introduced onto the fifth position of the benzene ring in sulfonylurea structures, as well as heterocyclic amino substituents (If-g) to seek a suitable soil degradation rate during such an in situ crop rotation system. Referring to the biological data and ScAHAS inhibition and ScAHAS docking results, they turned out to be AHAS inhibitors with high potent herbicidal activities. The various influence on soil degradation rate along with crop safety indicated that different substituents on the fifth position have exerted an apparent impact. Their united study of structure-activity-safety-degradation relationship has great potential to provide valuable information for further development of eco-friendly agrochemicals.

Research on the controllable degradation of: N -methylamido and dialkylamino substituted at the 5thposition of the benzene ring in chlorsulfuron in acidic soil

Owing to the lengthy residual problems associated with chlorsulfuron, metsulfuron-methyl, and ethametsulfuron, which prevents them from being used in the "annual multi-crop planting system", the application of these sulfonylurea herbicides (SU) has regrettably been terminated in China since 2014. In this field, we were the first to discover that the 5th position of the benzene ring in chlorsulfuron is a key point for influencing its degradation rate and the amino moiety at this position showed faster degradation rates and maintained their original potent bioactivity. In this study, we further elaborated on N-methylamido and dialkylamino substituents at the same position in chlorsulfuron to obtain 18 novel structures as M and N series. Their half-life degradation (DT50) values were faster, to varying degrees, than chlorsulfuron in acidic soil. It was found that most of the titled structures also retained their potent herbicidal activity and the crop safety of the M series towards corn greatly increased. Based on these data, a comprehensive graph describing the structure/degradation relationship was established first. Relating to the new molecules, their herbicidal activity (A), degradation rates (D), and crop safety (S) relationship were correlated and we used this approach to predict and explore the most preferable molecule, which coincided to the corresponding experimental data. The new concept of controllable degradation will provide us with more insight when searching for new ecological bioactive molecules in the future.

Development of Benzenesulfonamide Derivatives as Potent Glutathione Transferase Omega-1 Inhibitors

Glutathione transferase omega-1 (GSTO1-1) is an enzyme whose function supports the activation of interleukin (IL)-1β and IL-18 that are implicated in a variety of inflammatory disease states for which small-molecule inhibitors are sought. The potent reactivity of the active-site cysteine has resulted in reported inhibitors that act by covalent labeling. In this study, structure-activity relationship (SAR) elaboration of the reported GSTO1-1 inhibitor C1-27 was undertaken. Compounds were evaluated for inhibitory activity toward purified recombinant GSTO1-1 and for indicators of target engagement in cell-based assays. As covalent inhibitors, the kinact/KI values of selected compounds were determined, as well as in vivo pharmacokinetics analysis. Cocrystal structures of key novel compounds in complex with GSTO1-1 were also solved. This study represents the first application of a biochemical assay for GSTO1-1 to determine kinact/KI values for tested inhibitors and the most extensive set of cell-based data for a GSTO1-1 inhibitor SAR series reported to date. Our research culminated in the discovery of 25, which we propose as the preferred biochemical tool to interrogate cellular responses to GSTO1-1 inhibition.

MODULATORS OF INTRACELLULAR CHLORIDE CONCENTRATION

The present invention relates to a compound of Formula la, lb and Ic, (Formula Ia) a pharmaceutical composition comprising the same and their use in the treatment or prevention of pathological conditions associated to depolarizing GABAergic transmission including, for example, Down syndrome and autism.

Improved synthesis of the thiophenol precursor N-(4-chloro-3-mercaptophenyl)picolinamide for making the mGluR4 PET ligands

Recently [11C]mG4P012 (previously [11C]KALB012 and presently named as [11C]PXT012253 by Prexton Therapeutics) had been used as a biomarker during the preclinical development of a potential therapeutic drug, PXT0002331 (an mGluR4 PAM), for PD and L-dopa-induced dyskinesia. [11C]mG4P012 was shown to be a promising PET radioligand for mGluR4 in the monkey brain and for further development in human subjects. However, the previously reported multi-step synthesis of the thiophenol precursor suffered from low yields and difficult workup procedures. To support the translational research of [11C]mG4P012 and the other potential applications, we have developed a new route for synthesis of the thiophenol precursor and optimized the reaction conditions. The synthesis of N-(4-chloro-3-mercaptophenyl)picolinamide from 1-chloro-4-nitrobenzene has been greatly improved from 8% to 52% total yield with easy handling and in gram scales.

Dye intermediate (3-beta-hydroxyethylsulfonyl)aniline-4-aminoacetic acid and preparation method thereof

The invention relates to a dye intermediate (3-beta-hydroxyethylsulfonyl)aniline-4-aminoacetic acid and a preparation method thereof. The dye intermediate, (3-beta-hydroxyethylsulfonyl)aniline-4-aminoacetic acid, is represented as the structure formula (I). The preparation method includes the steps of: chlorosulfonation of 2-chloro-5-nitrobenzenesulfonic acid, reduction by sodium sulfite, hydroxyethylation, a condensation reaction with aminoacetic acid, hydrogenation reduction of the nitro group, and the like. The novel dye intermediate, compared with common dye intermediates, can greatly improve the water solubility of a dye, and reduces production cost and reduces environment pollution.

Dye intermediate namely (3-beta-hydroxyethylsulfonyl)aniline-4-aminobenzenesulfonic acid and preparation method thereof

The invention relates to a dye intermediate namely (3-beta-hydroxyethylsulfonyl)aniline-4-aminobenzenesulfonic acid and a preparation method thereof. The intermediate is (3-beta-hydroxyethylsulfonyl)aniline-4-aminobenzenesulfonic acid which has a structural formula as shown in a formula (I) in the specification. According to the invention, the dye intermediate is prepared through a series of preparation processes like chlorosulfonation of 2-chloro-5-nitrobenzenesulfonic acid, reduction with sodium sulfite, hydroxyethylation, a condensation reaction of the hydroxyethylated product and p-aminobenzenesulfonic acid, nitro hydrogenation reduction, etc. Compared with a common dye intermediate, the novel dye intermediate prepared by using the method provided by the invention can well improve water solubility of a prepared dye, and reduce production cost and environmental pollution.

Novel dye intermediate and active dye prepared from dye intermediate

The invention relates to a novel dye intermediate and active dye prepared from the dye intermediate. The dye intermediate has the structural formula shown as a formula in the accompanying drawing. The dye intermediate has the advantages that on the basis of meta-position oil of the common dye intermediate, para aminobenzoic acid is used for condensation, so that the goal of introducing the benzoyloxy is achieved. The color of the prepared dye is more vivid; the solubility is better.