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

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

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

• 17333-85-6 4-chlorophenyldiazonium salt 
• 108-90-7 chlorobenzene 
• 98-64-6 4-Chlorobenzenesulfonamide 
• 109-86-4 2-methoxy-ethanol 
• 5138-90-9 sodium 4-chlorobenzenesulfonate 
• 4911-58-4 5,5-dimethyl-hex-1-en-3-yne 
• 2901-92-0 p-chlorophenylsulfinyl chloride 
• 18387-62-7 1-(trimethylsilyl)-3-penten-1-yne 
• 349-89-3 p-chlorobenzenesulfonyl fluoride 
• 106-54-7 p-Chlorothiophenol 
• 7790-94-5 chlorosulfonic acid 
• 7664-93-9 sulfuric acid 
• 5184-71-4 4-methylphenyl-4-chlorophenyl sulfone 
• 15719-64-9 methylammonium carbonate 

Downstream Products

• 22771-98-8 N,N-Pentamethylen-4-chlorbenzol-sulfonamid 
• 32365-02-9 4-amino-N-(thiazol-2-yl)benzenesulfonamide 
• 99067-53-5 4-chloro-N-(thiazol-2-yl)benzenesulfonamide 
• 72-14-0 Sulfathiazole 
• 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) 
• 515-59-3 sulfamethylthiazole 
• 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 

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.

NEW SELECTIVE MODULATORS OF INSECT NICOTINIC ACETYLCHOLINE RECEPTORS

The present invention relates to a compound having the following formula (I): wherein: - A is a (hetero)aryl radical comprising from 5 to 10 carbon atoms, possibly substituted by at least one substituent chosen from the group consisting of: halogen atoms, amino, azido, cyano, nitro, hydroxyl, formyl, carboxyl, amido, (C1-C6)alkyl groups, halo(C1-C6)alkyl groups, (C1-C6)alkoxy groups, alkenyl groups, cycloalkenyl groups, and alkynyl groups, and - R is H, CN or CF3, or their pharmaceutically acceptable salts, racemates, diastereomers or enantiomers.

High yielding protocol for direct conversion of thiols to sulfonyl chlorides and sulfonamides

In this paper, a new method for oxidative chlorination of thiols to sulfonyl chlorides and sulfonamides using H2O2 in the presence of TMSCl is reported. The excellent yields, short reaction times, excellent efficiencies, low costs, and easy separation of products are the most important advantages of this method.

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.

Design, synthesis and biological evaluation of novel phenylsulfonylurea derivatives as PI3K/mTOR dual inhibitors

Five series of novel phenylsulfonylurea derivatives, 19a–d, 20a–d, 21a–d, 22a–d and 23a–d, bearing 4-phenylaminoquinoline scaffold were designed, synthesized and their IC50 values against four cancer cell lines (HepG-2, A549, PC-3 and MCF-7) were evaluated. Most compounds showed moderate cytotoxicity activity against the cancer cell lines. Structure–activity relationships (SARs) and pharmacological results indicated that introduction of 4-aminoquinoline scaffold and phenylsulfonylurea scaffold were beneficial for anti-tumor activity. Moreover, para-methoxyl substitution of 4-anilino moiety and para-halogen substitution of phenylsulfonylurea have different impacts on different series of compounds. Furthermore, the micromolecule group substitution in the 6-position of the quinoline ring have a slight impact on the cellular activity of the target compounds.

Sulfonyl halide synthesis by thiol oxyhalogenation using NBS/NCS – iPrOH

A rapid and facile method provides a general route to sulfonyl bromides/chlorides by the oxidation of thiols using NXS – ROH (X?=?Br,Cl, R?=?iPr) as an oxyhalogenation reagent. Control experiments suggest that the alcohol component is the source of oxygen. The proposed method enable the access to structurally diverse sulfonyl bromides and chlorides including challenging examples, inaccessible by other synthetic methods.

Conversion of thiols into sulfonyl halogenides under aerobic and metal-free conditions

An environmentally benign, metal-free synthesis of sulfonyl chlorides and bromides from thiols in the presence of ammonium nitrate, an aqueous solution of HCl and HBr and oxygen as a terminal oxidant was developed. The reactivity of various substituted thiophenols, benzylic-, aliphatic- and heteroaromatic thiols was examined. Ammonium nitrate served as a source of nitrogen oxides (NO/NO2), which are the crucial players in a redox-catalytic cycle. Sulfonyl chlorides and bromides were isolated without extraction and "filtered" over a short pad of silica gel; the use of solvents was greatly reduced in comparison with traditional isolation and purification. A "one-pot" protocol for the conversion of thiol into sulfonamide is also demonstrated. Scale-up experiments on the preparation of sulfonyl chloride and bromide are shown. A possible reaction pathway is discussed.

The sulfonylurea-containing structure of the preparation and application of zola non-nepal derivatives (by machine translation)

The invention discloses a sulfonylurea structure containing sorafenib derivative, its geometric isomer and pharmaceutically acceptable salt, hydrate, solvate or prodrug, and application thereof in preparation of drugs treating and/or preventing hyperplastic diseases, application in preparation of drugs treating and/or preventing cancers, and application in preparation of drugs treating and/or preventing lung cancer, liver cancer, gastric cancer, colon cancer and breast cancer.

Aromatic Chlorosulfonylation by Photoredox Catalysis

Visible-light photoredox catalysis enables the efficient synthesis of arenesulfonyl chlorides from anilines. The new protocol involves the convenient in situ preparation of arenediazonium salts (from anilines) and the reactive gases SO2and HCl (from aqueous SOCl2). The photocatalytic chlorosulfonylation operates at mild conditions (room temperature, acetonitrile/water) with low catalyst loading. Various functional groups are tolerated (e.g., halides, azides, nitro groups, CF3, SF5, esters, heteroarenes). Theoretical and experimental studies support a photoredox-catalysis mechanism.