4533-95-3

Basic information

• Product Name: 2-Chloro-5-nitro-benzenesulfonyl chloride
• Synonyms: 2-chloro-5-nitrobenzenesulphonyl chloride;2-Chlor-5-nitrobenzolsulfonylchlorid;2-Chloro-5-nitro-benzenesulfonyl chloride;2-chloro-5-nitrobenzene-1-sulfonyl chloride;NSC 350627
• CAS NO: 4533-95-3
• Molecular Formula: C₆H₃Cl₂NO₄S
• Molecular Weight: 256.06
• EINECS: 224-873-4
• Product Categories: Benzene derivates;Sulfonyl Chlorides
• Mol File: 4533-95-3.mol
• Article Data: 41

Chemical Properties

• Melting Point: 88-90°C
• Boiling Point: 371.6 °C at 760 mmHg
• Flash Point: 178.5 °C
• Appearance: Solid
• Density: 1.708 g/cm³
• Vapor Pressure: 2.19E-05mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Dichloromethane, Ether, Ethyl Acetate
• CAS DataBase Reference: 2-Chloro-5-nitro-benzenesulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-5-nitro-benzenesulfonyl chloride(4533-95-3)
• EPA Substance Registry System: 2-Chloro-5-nitro-benzenesulfonyl chloride(4533-95-3)

Safety Data

• RIDADR: UN3261
• Hazardous Substances Data: 4533-95-3(Hazardous Substances Data)

Usage

Description

2-Chloro-5-nitro-benzenesulfonyl chloride, with the CAS number 4533-95-3, is a solid compound that plays a significant role in organic synthesis. It is characterized by its unique chemical structure, which includes a chlorine atom at the 2nd position and a nitro group at the 5th position on a benzene ring, with a sulfonyl chloride group attached to the sulfur atom.

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

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

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 articles and documents

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.

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.

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.