133-59-5

Usage

Uses

Used in Organic Synthesis:
O-Toluenesulfonyl chloride is used as a reagent in organic synthesis for the formation of various chemical compounds. It is particularly useful in the protection of functional groups, such as alcohols and amines, during complex organic reactions, preventing unwanted side reactions and facilitating the selective formation of target molecules.
Used in Pharmaceutical Industry:
O-Toluenesulfonyl chloride serves as a pharmaceutical intermediate, playing a crucial role in the synthesis of various drugs. Its ability to form stable derivatives with active pharmaceutical ingredients allows for the development of new drugs with improved properties, such as enhanced stability, solubility, and bioavailability.
Used in Saccharin Production:
In the chemical industry, O-Toluenesulfonyl chloride is utilized in the production of saccharin, an artificial sweetener. Its use in this process highlights its importance in the synthesis of compounds with applications in the food and beverage industry.
Used in Synthesis of Specific Compounds:
O-Toluenesulfonyl chloride is also employed in the synthesis of specific compounds, such as oxazolinemesityl o-tolyl sulfone, o-toluenesulfonate, 2-methyl-4′-t-butyldiphenyl sulfone, and 5-chloro-3-phenyl-2,1-benzisoxazole. These compounds have various applications in different fields, including pharmaceuticals, materials science, and chemical research.

InChI:InChI=1/C7H7ClO2S/c1-6-4-2-3-5-7(6)11(8,9)10/h2-5H,1H3

Upstream product

• 108-88-3 toluene 
• 64846-49-7 1-Methoxymethylsulfanyl-2-methyl-benzene 
• 82125-34-6 N,N-diethylthiocarbamic acid S-o-tolyl ester 
• 137-06-4 2-thiocresol 
• 7790-94-5 chlorosulfonic acid 
• 7446-70-0 aluminium trichloride 
• 7705-08-0 iron(III) chloride 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 13165-77-0 toluenesulfinic acid 
• 7732-18-5 water 
• 7782-50-5 chlorine 
• 5153-67-3 nitrostyrene 
• 2028-34-4 o-toluene-diazonium chloride 
• 88-19-7 methyl 2-(aminosulfonyl)benzoate 

Downstream Products

• 872283-93-7 1-(toluene-2-sulfonyl)-1H-indazole 
• 861360-95-4 2-(toluene-2-sulfonyl)-2H-indazole 
• 113037-90-4 8-ethoxy-1-(toluene-2-sulfonyl)-quinolinium; chloride 
• 19829-14-2 N-(2-hydroxy-ethyl)-toluene-2-sulfonamide 
• 93718-74-2 toluene-2-sulfonic acid m-tolyl ester 
• 24415-29-0 toluene-2-sulfonic acid o-tolyl ester 
• 56776-55-7 N-phenyl-S-(2-methylphenyl) sulfonamide 
• 1071550-24-7 N-cyano-N'-(toluene-2-sulfonyl)-guanidine 
• 18271-18-6 N-(2-naphthyl)-p-toluenesulphonamide 
• 41908-97-8 o-tolyl-p-tolyl sulfone 
• 106475-33-6 toluene-2-sulfonic acid-(4-bromo-anilide) 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 92190-68-6 toluene-2-sulfonic acid p-tolyl ester 
• 101746-79-6 (4-t-butylphenyl)-o-tolyl sulfone 

Relevant academic research and scientific papers

Preparation method of substituted benzene sulfonyl chloride

The invention provides a preparation method of substituted benzene sulfonyl chloride, which comprises the following steps: carrying out diazotization reaction on an aniline compound with a structure as shown in a formula I to obtain fluoboric acid diazonium salt with a structure as shown in a formula II; obtaining substituted benzene sulfonyl chloride with a structure as shown in a formula III from the fluoboric acid diazonium salt with the structure as shown in the formula II; wherein R is selected from any one of ortho-chlorine, bromine, methyl, chloromethyl, bromomethyl, nitro, cyano, acetyl, meta-chlorine, bromine, methyl, chloromethyl, bromomethyl, nitro, cyano, acetyl, para-chlorine, bromine, methyl, chloromethyl, bromomethyl, nitro, cyano and acetyl. The preparation method of the substituted benzene sulfonyl chloride provided by the invention is simple in reaction process, easy to operate, ideal in effect and suitable for industrial production.

CHEMICAL COMPOUNDS

The present disclosure describes novel compounds, or their pharmaceutically acceptable salts, pharmaceutical compositions containing them, and their medical uses. The compounds of the disclosure have activity as Janus kinase (JAK) inhibitors and are useful in the treatment or control of inflammation, auto-immune diseases, cancer, and other disorders and indications where modulation of JAK would be desirable. Also described herein are methods of treating inflammation, auto-immune diseases, cancer, and other conditions susceptible to inhibition of JAK by administering a compound herein described.

Sulfonamide compound as well as preparation method and application thereof

The invention discloses a sulfonamide compound as well as a preparation method and application thereof. Three kinases including EGFR, VEGFR-2 and FGFR1 are used as targets; chalcone is used as a primer; an alpha,beta-unsaturated carbonyl conjugated struct

Selective Late-Stage Sulfonyl Chloride Formation from Sulfonamides Enabled by Pyry-BF4

Reported here is a simple and practical functionalization of primary sulfonamides, by means of a pyrylium salt (Pyry-BF4), with nucleophiles. This simple reagent activates the poorly nucleophilic NH2 group in a sulfonamide, enabling the formation of one of the best electrophiles in organic synthesis: a sulfonyl chloride. Because of the variety of primary sulfonamides in pharmaceutical contexts, special attention has been focused on the direct conversion of densely functionalized primary sulfonamides by a late-stage formation of the corresponding sulfonyl chloride. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides, sulfonates, sulfides, sulfonyl fluorides, and sulfonic acids. The mild reaction conditions and the high selectivity of Pyry-BF4 towards NH2 groups permit the formation of sulfonyl chlorides in a late-stage fashion, tolerating a preponderance of sensitive functionalities.

Propanolysis of arenesulfonyl chlorides: Nucleophilic substitution at sulfonyl sulfur

We have studied the mechanism of solvolysis of arenesulfonyl chlorides by propan-1-ol and propan-2-ol at 303-323 K. Kinetic profiles were appropriately fit by first-order kinetics. Reactivity increases with electron-donating substituents. Ortho-alkyl substituted derivatives of arenesulfonyl chlorides show increased reactivity, but the origin of this “positive” ortho-effect remains unclear. Likely, ortho-methyl groups restrict rotation around the C-S bond, facilitating the attack of the nucleophile. No relevant reactivity changes have been found with propan-1-ol and propan-2-ol in terms of nucleophile steric effect. The existence of isokinetic relationships for all substrates suggests a single mechanism for the series. Solvolysis reactions of all substrates in both alcohols show isokinetic temperatures (Tiso) close to the working temperature range, which is an evidence of the process being influenced by secondary reactivity factors, likely of steric nature in the TS. Solvation plays a relevant role in this reaction, modulating the reactivity. In some cases, the presence of t-Bu instead of Me in para- position leads to changes in the first solvation shell, increasing the energy of the reaction (ca. 1?kJ·mol?1). The obtained results suggest the same kinetic mechanism of solvolysis of arenesulfonyl chlorides for propan-1-ol and propan-2-ol, as in MeOH and EtOH, where bimolecular nucleophilic substitution (SN2) takes place with nucleophilic solvent assistance of one alcohol molecule and the participation of the solvent network involving solvent molecules of the first solvation shell.

Aminoxidation of Arenethiols to N-Chloro-N-sulfonyl Sulfinamides

A simple and efficient method to synthesize N-chloro-N-sulfonylsulfinamides by the direct aminoxidation of arenethiols under aqueous and mild conditions is disclosed, geminally installing the oxo and amino groups on the sulfur atom of arenethiols. The products have been primarily developed as sulfinylation reagents to convert Grignard reagents into sulfoxides, and as amination reagents to convert secondary amines into hydrazine derivatives.

Synthesis of aryl sulfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids

A palladium-catalyzed method for the preparation of sulfonamides is described. The process exhibits significant functional group tolerance and allows for the preparation of a number of arylsulfonyl chlorides and sulfonamides under mild conditions.

Phenylenediamine urotensin-II receptor antagonists and CCR-9 antagonists

The present invention relates to urotensin II receptor antagonists, CCR-9 antagonists, pharmaceutical compositions containing them and their use.

Reaction of arendiazonium salts and SO2with α-nitroolefins

In reaction of β-nitrostyrene and 2-(2-nitrovinyl)furan with arenediazonium chlorides and SO2 in the presence of copper(II) chloride products were obtained resulting from addition of arylsulfonyl group and a hydrogen atom across the C=C bond: 2-nitro-1-phenylethylsulfonylarenes and 2-(1-arylsulfonyl-2-nitroethyl)furans respectively. An anion-radical mechanism of the reaction was suggested.

Low molecular weight dendritic compounds as pharmaceutical agents

This invention is for low molecular weight dendritic polymers (dendroids) of Formula I are useful as agents in the treatment of cancer, Alzheimers disease, thrombosis, inflammatory diseases, and bacterial resistance.