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

• 98-64-6 4-Chlorobenzenesulfonamide 
• 18387-62-7 1-(trimethylsilyl)-3-penten-1-yne 
• 2901-92-0 p-chlorophenylsulfinyl chloride 
• 106-54-7 p-Chlorothiophenol 
• 5184-71-4 4-methylphenyl-4-chlorophenyl sulfone 
• 15719-64-9 methylammonium carbonate 
• 2751-25-9 p-chlorophenylsulfonyl hydrazide 
• 1146-44-7 4,4'-dichlorophenyl thiosulfonate 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 127-65-1 chloroamine-T 
• 29917-04-2 sodium chloro((4-nitrophenyl)sulfonyl)amide 
• 30066-82-1 N-chloro-p-chlorobenzenesulfonamide sodium salt 
• 127-52-6 chloramine-B 
• 29917-03-1 N-chloro-p-methoxybenzenesulfonamide sodium salt 

Downstream Products

• 22771-98-8 N,N-Pentamethylen-4-chlorbenzol-sulfonamid 
• 32365-02-9 4-amino-N-(thiazol-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 
• 56799-95-2 N-(1-naphthyl)-4-chlorobenzenesulfonamide 
• 4279-74-7 N-(4-methylphenyl)-4-chlorobenzene sulfonamide 
• 599-87-1 4-chloro-N-(4-chlorophenyl)benzenesulfonamide 
• 7455-05-2 4-chloro-N-(4-methoxyphenyl)benzenesulfonamide 
• 51012-31-8 2-((4-chlorophenyl)sulfonamido)benzoic acid 
• 60893-38-1 1-chloro-4-((4-methoxyphenyl)sulfonyl)benzene 
• 18113-54-7 4-methoxyphenyl 4-chlorobenzenesulfonate 

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.

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.

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.