98-60-2

Basic information

• Product Name: 4-Chlorobenzenesulfonyl chloride
• Synonyms: 4-chloro-benzenesulfonicacichloride;4-chloro-benzenesulfonylchlorid;Benzenesulfonyl chloride, 4-chloro-;Benzenesulfonyl chloride, p-chloro-;Benzenesulfonylchloride,4-chloro-;Chlorid kyseliny p-chlorbensulfonove;chloridkyselinyp-chlorbensulfonove;chloridkyselinyp-chlorbensulfonove(czech)
• CAS NO: 98-60-2
• Molecular Formula: C₆H₄Cl₂O₂S
• Molecular Weight: 211.07
• EINECS: 202-685-3
• Product Categories: Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds
• Mol File: 98-60-2.mol
• Article Data: 53

Chemical Properties

• Melting Point: 50-52 °C(lit.)
• Boiling Point: 141 °C15 mm Hg(lit.)
• Flash Point: 226 °F
• Appearance: Clear/Liquid
• Density: 1.5075 (estimate)
• Vapor Pressure: 0.00995mmHg at 25°C
• Refractive Index: 1.569
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: soluble in Toluene
• Water Solubility: INSOLUBLE
• Sensitive: Moisture Sensitive
• BRN: 511583
• CAS DataBase Reference: 4-Chlorobenzenesulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chlorobenzenesulfonyl chloride(98-60-2)
• EPA Substance Registry System: 4-Chlorobenzenesulfonyl chloride(98-60-2)

Safety Data

• Hazard Codes: C
• Statements: 34-37
• Safety Statements: 26-28-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 2
• RTECS: DB8925000
• F: 21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 98-60-2(Hazardous Substances Data)

Usage

Description

4-Chlorobenzenesulfonyl chloride is an organic compound with the chemical formula C6H4Cl(SO2Cl). It is a derivative of benzene, where a chlorine atom is attached to the 4th position and a sulfonyl chloride group is attached to the benzene ring. 4-Chlorobenzenesulfonyl chloride is a white crystalline solid and is soluble in organic solvents.

Uses

Used in Organic Synthesis:
4-Chlorobenzenesulfonyl chloride is used as a reagent in the synthesis of various organic compounds. It is particularly useful in the synthesis of precursors for the generation of 3,4-pyridyne, a highly reactive molecule with potential applications in the formation of novel heterocycles and other complex organic structures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Chlorobenzenesulfonyl chloride is used as an intermediate in the synthesis of various drug molecules. Its unique chemical properties allow it to be a versatile building block for the development of new pharmaceutical agents with potential therapeutic applications.
Used in Chemical Research:
4-Chlorobenzenesulfonyl chloride is also used in chemical research as a model compound to study the reactivity and properties of sulfonyl chloride-containing molecules. This helps researchers to better understand the behavior of similar compounds and develop new synthetic strategies and applications.

Synthesis Reference(s)

The Journal of Organic Chemistry, 7, p. 15, 1942 DOI: 10.1021/jo01195a003

Purification Methods

Crystallise it from ether in powdered Dry-Ice, after the solution has been washed with 10% NaOH until colourless and dried (Na2SO4). Distil it in vacuo and store it in the absence of H2O. [Beilstein 11 IV 114.]

InChI:InChI=1/C6H4Cl2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H

Upstream product

• 349-89-3 p-chlorobenzenesulfonyl fluoride 
• 106-54-7 p-Chlorothiophenol 
• 7790-94-5 chlorosulfonic acid 
• 7664-93-9 sulfuric acid 
• 108-90-7 chlorobenzene 
• 5184-71-4 4-methylphenyl-4-chlorophenyl sulfone 
• 15719-64-9 methylammonium carbonate 
• 98-66-8 4-chloro-benzenesulfonic acid 
• 5138-90-9 sodium 4-chlorobenzenesulfonate 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 29411-04-9 S-(4-chlorophenyl) methylcarbamothioate 
• 21021-60-3 S-acetyl-4-chlorothiophenol 
• 106-47-8 4-chloro-aniline 
• 15151-78-7 ethyl S-(4-chlorophenyl) thiolcarbonate 

Downstream Products

• 22771-98-8 N,N-Pentamethylen-4-chlorbenzol-sulfonamid 
• 32365-02-9 4-amino-N-(thiazol-2-yl)benzenesulfonamide 
• 1213-38-3 4-chloro-N-pyridin-2-yl-benzenesulfonamide 
• 99074-46-1 4-chloro-N-pyrimidin-2-yl-benzenesulfonamide 
• 349403-80-1 4-chloro-benzenesulfonic acid-(4-methyl-[2]pyridylamide) 
• 35607-89-7 N-benzooxazol-2-yl-4-chloro-benzenesulfonamide 
• 301683-40-9 R₅₃,643-1 
• 858498-77-8 4-chloro-benzenesulfonic acid-(4-methoxy-pyrimidin-2-ylamide) 
• 92696-62-3 4-chloro-benzenesulfonic acid-(5-isobutyl-[1,3,4]thiadiazol-2-ylamide) 
• 16387-86-3 5-(4-chloro-benzenesulfonyloxy)-benzo[1,3]dioxole 
• 859486-36-5 2-(4-chloro-benzenesulfonylamino)-thiazole-5-carboxylic acid ethyl ester 
• 56799-95-2 N-(1-naphthyl)-4-chlorobenzenesulfonamide 
• 4279-74-7 N-(4-methylphenyl)-4-chlorobenzene sulfonamide 

Relevant articles and documents

Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides

A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.

Preparation method of medical intermediate of parachlorobenzenesulfonyl chloride

The invention discloses a preparation method of a medical intermediate of parachlorobenzenesulfonyl chloride. The preparation method specifically comprises the following steps: firstly, cyclodextrin is modified sequentially through maleic anhydride and tetradecyl trimethyl ammonium chloride, and the modified cyclodextrin is obtained; and then a reaction is conducted by adopting sodium 4-chlorobenzenesulfonate and thionyl chloride as raw materials and the modified cyclodextrin as a catalyst, and by being added with ammonium trifluoroacetate for assisting. The prepared medical intermediate of the parachlorobenzenesulfonyl chloride is high in yield and high in purity, the reacting conditions are easy to operate, the requirements for equipment are low, and control is easy.

Preparation method of 4-chlorothiophenol

The invention relates to a simple preparation method of 4-chlorothiophenol. 4-chlorobenzenesulfonyl chloride is prepared from sodium 4-chlorobenzenesulfonate and thionyl chloride as raw materials andtoluene as a solvent through a reaction at 50-70 DEG C for 3-5 h under the action of a phase transfer catalyst and reduced by iron powder at the temperature of 40-60 DEG C under an acidic condition, and 4-chlorothiophenol is obtained. The method has the characteristics of being low in cost, simple and convenient to operate and suitable for industrial production.