54997-90-9

Basic information

• Product Name: 4-ISOPROPYLBENZENESULFONYL CHLORIDE
• Synonyms: 4-ISOPROPYLBENZENESULFONYL CHLORIDE;4-ISOPROPYLBENZENESULPHONYL CHLORIDE;AKOS B019384;ART-CHEM-BB B019384;Cumene-4-sulphonyl chloride;4-Isopropyl Benzensulfonyl Chloride;4-ISOPROPYLBENZENESULFONYL CHLORIDE, TECH GRADE;Cumene-4-sulfonylchloride
• CAS NO: 54997-90-9
• Molecular Formula: C₉H₁₁ClO₂S
• Molecular Weight: 218.7
• EINECS: -0
• Product Categories: Boron, Nitrile, Thio,& TM-Cpds;Benzene derivates;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds
• Mol File: 54997-90-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 51-52 °C
• Boiling Point: 142-143 °C (12 mmHg)
• Flash Point: 143 °F
• Appearance: clear yellow to orange liquid
• Density: 1.220 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00568mmHg at 25°C
• Refractive Index: n20/D 1.5410(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive: Moisture Sensitive
• BRN: 1103862
• CAS DataBase Reference: 4-ISOPROPYLBENZENESULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ISOPROPYLBENZENESULFONYL CHLORIDE(54997-90-9)
• EPA Substance Registry System: 4-ISOPROPYLBENZENESULFONYL CHLORIDE(54997-90-9)

Safety Data

• Hazard Codes: C
• Statements: 34-29
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 54997-90-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4-Isopropylbenzenesulfonyl chloride is used as a reagent for the synthesis of chlorosulfonyl-functionalized ATRP (Atom transfer radical polymerization) initiator. This initiator is essential in the controlled polymerization of various monomers, leading to the formation of well-defined polymers with specific molecular weights and architectures.
Additionally, 4-Isopropylbenzenesulfonyl chloride is used as a precursor in the synthesis of 4-isopropylbenzenethiol, which is an important intermediate in the production of various organic compounds and pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Isopropylbenzenesulfonyl chloride is used as a key intermediate in the synthesis of various drugs and drug candidates. Its unique chemical properties allow for the development of novel therapeutic agents with specific biological activities.
Used in Polymer Science:
In the field of polymer science, 4-Isopropylbenzenesulfonyl chloride is used as a building block for the development of new polymer materials with tailored properties. These materials can be utilized in various applications, such as coatings, adhesives, and composites, due to their unique mechanical, thermal, and chemical properties.

InChI:InChI=1/C9H11ClO2S/c1-7(2)8-3-5-9(6-4-8)13(10,11)12/h3-7H,1-2H3

Upstream product

• 219741-32-9 4-isopropylbenzenesulfonyl hydrazide 
• 4946-14-9 4-mercapto-cumene 
• 98-82-8 Isopropylbenzene 
• 16066-35-6 p-cumenesulfonic acid 

Downstream Products

• 883993-19-9 allyl-{2-[4-(4-isopropyl-benzenesulfonylamino)-phenyl]-ethyl}-carbamic acid tert-butyl ester 
• 883992-82-3 4-isopropyl-N-[4-(1-propyl-pyrrolidin-2-ylmethyl)-phenyl]-benzenesulfonamide 
• 883994-20-5 [(R)-5-(4-isopropyl-benzenesulfonylamino)-indan-2-yl]-propyl-carbamic acid tert-butyl ester 
• 1080637-31-5 methyl 4-(4-isopropylphenylsulfonyl)-3-oxobutanoate 
• 859832-43-2 1-(4-isopropylbenzenesulfonyl)-3-(1-methylpyrrolidin-3-yl)-5-methoxy-1H-indole 
• 859832-34-1 1-(4-isopropylbenzenesulfonyl)-3-(4-chloro-1-methyl-2,5-dihydro-1H-pyrrol-3-yl)-5-methoxy-1H-indole 
• 321707-31-7 4-isopropyl-N-(prop-2-ynyl)benzenesulfonamide 
• 959395-92-7 C₂₃H₂₉N₃O₂S 
• 1039308-36-5 C₂₂H₂₇N₃O₂S 

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.

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.

Ring inversion dynamics of derivatives of thianthrene di- and tetraoxide

The ring inversion barrier for thianthrene tetraoxide was determined by making use of the variable temperature 13C NMR spectra of the 2,7-diisopropyl derivative (ΔG? = 6.5 kcal mol-1). The barrier is lower than that measured for a trans thianthrene dioxide derivative (ΔG? = 9.35 kcal mol-1). These results agree well with ab initio theoretical predictions.

Structure-activity relationships in platelet-activating factor (PAF). 11-From PAF-antagonism to phospholipase A2 inhibition: Syntheses and structure-activity relationships in 1-arylsulfamido-2-alkylpiperazines

1-Benzoyl-2-alkyl piperazines are strong inhibitors of Group I and II secreted PLA2s. An improvement of their activity was obtained by replacing the amide function by a sulfamide and by introduction of electrodonor substituents on the para position of the benzenesulfonyl moiety. Neither the position on one of the carbon of the piperazine ring nor the absolute configuration of this carbon have an effect on the affinity for one or the other group of PLA2, but the lipophilicity remains for these series an essential parameter. In addition structure-activity relationships allow new hypothesis on interaction of these piperazine derivatives with the catalytic site of PLA2s.

Use of N-(4-aryl-thiazol-2-yl)-sulfonamides

The invention is concerned with the use of sulfonamide derivatives of the general formula STR1 wherein R signifies lower-alkyl, phenyl, benzyl, naphthyl, pyridyl or thienyl, optionally substituted by one or more lower-alkyl, lower-alkoxy, lower-alkyl carb

REAGENTS FOR 2-TETRAHYDROTHIENYL AND 2-TETRAHYDROTHIOPYRANYL CATIONS

O- and S-2-tetrahydrothienyl and 2-tetrahydropyranyl ethers were obtained by reaction of primary alcohols, phenols, and arenethiols with 1-p-toluenesulphonyliminotetrahydrofuran and 1-p-toluenesulphonyliminotetrahydrothiopyran in the presence of sodium hydride in dimethylformamide or by acid-catalysed transacetalysation of 2-methoxytetrahydrothiophene and 2-methoxytetrahydrothiopyran with secondary alcohols and arenethiols.

Novel copolymers and superoxide dismutase modified with said copolymers

Described are copolymers comprising the copolymer--constituting units characterized in the claims and having an average molecular weight of 400 to 20,000. Furthermore superoxide dismutase (SOD) derivatives are described which can be obtained by modification with the above copolymers and have a single chemical structure, retain most of the enzymatic activity of SOD and exhibit a much prolonged plasma half-life. Therefore, they are useful as medicinal chemicals.

Substituent effects on benzyl radical hyperfine coupling (hfc) constants. Part 3. Comparison of the α-hfc for substituted benzyl radicals with the β-hfc for substituted cumyl radicals

The electron spin resonance (esr) spectra of eighteen para-substituted cumyl radicals were analyzed.The relationship between the β-hyperfine coupling (β-hfc) constants of these cumyl radicals and the corresponding α-hfc constants of benzyl radicals was studied.Although there is a general trend for the α- and β-hfc values to vary in a similar manner, specific deviations from a linear correlation between these parameters were observed.These deviations were rationalized by considering charge effects on spin delocalization.The correlation coefficient for the linear regression analysis of these α- and β-hfc values was found to significantly improve when parameters reflecting charge effects on spin delocalization were included in an extended Hammett treatment of the spectral data.

SULFONATION OF CUMENE WITH SULFURIC AND HALOGENOSULFONIC ACIDS

The sulfonation of cumene by sulfuric and chloro- and fluorosulfonic acids in the range of 0-100 deg C under heterogenous and heterogenous-homogenous conditions gives mixtures of isomeric sulfonyl halides and/or sulfonic acids, in which the para isomer predominates (90-95percent of the total isomers at temperatures above 75 deg C and/or with the addition of the sulfonating agent to the cumene).If the reagents are mixed in the opposite order and at low temperatures (0-25 deg C), the proportion of the ortho isomer in the mixture of sulfo products increases to 20-22percent.The yield of the sulfonyl halides show an extremal relationship with temperature.The composition of the sulfonic acids and their halides formed under the conditions of a single experiment with the halogenosulfonic acids differ as a result, probably, of the nonequilibrium nature of the process and of the presence of several paths to the formation of the acid halides.