4533-96-4

Basic information

• Product Name: 4-CHLORO-2-NITROBENZENESULFONYL CHLORIDE
• Synonyms: BENZENESULFONYL CHLORIDE, 4-CHLORO-2-NITRO-;4-CHLORO-2-NITROBENZENESULFONYL CHLORIDE;4-chloro-2-nitrophenylsulphonyl chloride;4-Chloro-2-nitrophenylsulfonylchloride;4-chloro-2-nitrobenzene-1-sulfonyl chloride;4-Chloro-2-nitrobenzenesulfonyl chloride 97%
• CAS NO: 4533-96-4
• Molecular Formula: C₆H₃Cl₂NO₄S
• Molecular Weight: 256.06
• EINECS: 224-875-5
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 4533-96-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 75-79°C
• Boiling Point: 352.7 °C at 760 mmHg
• Flash Point: >110℃
• Appearance: /
• Density: 1.708 g/cm³
• Vapor Pressure: 7.69E-05mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Sensitive: Moisture Sensitive
• Stability: Hygroscopic
• CAS DataBase Reference: 4-CHLORO-2-NITROBENZENESULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2-NITROBENZENESULFONYL CHLORIDE(4533-96-4)
• EPA Substance Registry System: 4-CHLORO-2-NITROBENZENESULFONYL CHLORIDE(4533-96-4)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8 / PGII
• WGK Germany: 1
• HazardClass: 8
• Hazardous Substances Data: 4533-96-4(Hazardous Substances Data)

Usage

General Description

4-CHLORO-2-NITROBENZENESULFONYL CHLORIDE is a chemical compound with the molecular formula C6H4ClNO4SCl. It is a chlorinated nitrobenzenesulfonyl chloride that is used in the synthesis of various pharmaceuticals and agrochemicals. It is a highly reactive and toxic compound, and it is primarily used as a reagent in organic synthesis. It is commonly employed in the production of sulfonamides, which are important classes of antibiotics. Additionally, it is utilized in the manufacturing of dyes, pigments, and other specialty chemicals. Due to its reactivity and potential health hazards, it must be handled with care and in a well-ventilated environment with appropriate protective equipment.

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

Upstream product

• 345-18-6 2-fluoro-5-chloronitrobenzene 
• 89-63-4 4-Chloro-2-nitroaniline 
• 855294-59-6 thiobenzoic acid S-(4-chloro-2-nitro-phenyl ester) 
• 2050-66-0 bis(2-nitro-4-chlorophenyl)disulfide 
• 27165-22-6 2-nitro-4-chlorobenzenediazonium cation 

Downstream Products

• 2719-66-6 4-chloro-2-nitro-benzenesulfinic acid 
• 1227476-15-4 Azobenzene 
• 92-87-5 p,p'-diaminobiphenyl 
• 51144-97-9 1-(4-chloro-2-nitrobenzenesulfonyl)-1H-pyrrole 
• 1015689-24-3 4-(2-Amino-4-chloro-benzenesulfonylamino)-piperidine-1-carboxylic acid tert-butyl ester 
• 1605279-99-9 3-benzyl-8-chloro-1H-benzo[e]imidazo[1,2-b][1,2,4]thiadiazin-2(3H)-one-5,5-dioxide 
• 1581289-10-2 C₁₅H₁₄ClN₃O₄S 
• 1228352-69-9 C₂₀H₁₈ClN₉O₉S₂ 
• 1013759-91-5 2-amino-4-chloro-N-quinolin-8-yl-benzenesulfonamide 
• 568585-36-4 N-(2-aminoethyl)-2-chloro-4-nitro-benzenesulfonamide acetic acid salt 
• 568585-27-3 N-(2-aminoethyl)-4-chloro-2-nitro-benzenesulfonamide acetic acid salt 
• 325724-69-4 2-chloro-5-(2-chloroanilinosulphonyl)aniline 
• 132749-70-3 N-(2-bromophenyl)-N-methyl-2-(acetylamino)-4-chlorobenzenesulfonamide 
• 132749-61-2 N-(2-bromophenyl)-2-(acetylamino)-4-chlorobenzenesulfonamide 

Relevant articles and documents

A process for the preparation of substituted benzene sulfonyl chloride

The invention provides a preparation method of a pesticide intermediate, and in particular relates to a preparation method of substituted benzene sulfonyl chloride. The preparation method comprises the following steps: by taking substituted aniline as a raw material, first, carrying out diazo-reaction with sodium nitrite; then, carrying out chlorosulfonation with thionyl chloride aqueous liquor containing a catalyst to prepare substituted benzene sulfonyl chloride, wherein the yield ranges from 78% to 91%. The preparation method provided by the invention simplifies the reaction step, is safe to operate, mild in reaction conditions which are easy to control and low in equipment demand, the yield is improved, the production cost is lowered, emission of the three wastes is reduced, and the environment-friendly load is reduced, so that the preparation method is suitable for industrialized production.

Aqueous process chemistry: The preparation of aryl sulfonyl chlorides

The use of aqueous acidic conditions for the preparation of arylsulfonyl chlorides from diazonium salts in the presence of copper salts, preferably CuCl, together with thionyl chloride as the sulfur dioxide source, has considerable advantages over recommended literature procedures, whereby reactions are carried out in acetic acid with minimisation of water content of the solvent. The method has been shown to be successful for a wide range of electron-deficient and electron-neutral aryl substrates. The sulfonyl chlorides are protected from hydrolysis by their low solubility in water, which results in their direct precipitation from the reaction mixture in good yields (>70%) and high strength (>98% w/w). The aqueous process, which is additionally safer and more robust, can be readily scaled up and has significant environmental benefits.

Novel benzopyridothiadiazepines as potential active antitumor agents

The synthesis of novel thiadiazepine derivatives, that could be considered as constraint analogues of E-7010, are reported. These molecules were evaluated for their antiproliferative activity toward the murine L1210 leukemia cell line. Flow cytometric studies performed on L1210 cells with the most cytotoxic compounds showed an accumulation of the cells in the G2/M phases of the cell cycle with a significant percentage of tetraploid cells (8N DNA content). Submicromolar cytotoxicities were observed with compounds 2b, 4b, 4e, 4g, and 4i. Two of them, compounds 2b and 4b, were found to be potent inhibitors of tubulin polymerization with IC50 of respectively 3.8 and 2.4 μM compared to 2.4 μM for desoxypodophyllotoxin. A 4-methoxyphenylethyl substitution on the pyridinyl nitrogen of the benzopyridothiadiazepine was found to be essential for the antiproliferative activity. The in vitro activities of compounds 2b and 4b make benzopyridothiadiazepine dioxides a promising new class of tubulin binders which warrant further in vivo evaluation.