1899-93-0

Usage

Uses

1. Used in Pharmaceutical Industry:
m-Toluenesulfonyl chloride is used as a reactant for the synthesis of biologically active molecules. It plays a crucial role in the production of small molecule ligands for the Stat3 SH2 domain, which are essential in the development of drugs targeting various diseases.
2. Used in Antibacterial Applications:
In the field of antibacterial research, m-Toluenesulfonyl chloride is used as a reactant to synthesize aryldisulfonamides. These compounds exhibit potent antibacterial activity, making them valuable in the development of new antibiotics to combat drug-resistant bacteria.
3. Used in Treatment of Gaucher Disease:
m-Toluenesulfonyl chloride is employed as a reactant in the synthesis of quinazoline analogs, which are used for the treatment of Gaucher disease. Gaucher disease is a rare genetic disorder that affects the body's ability to break down a specific type of fat, leading to a buildup of fatty substances in the spleen, liver, and other organs. The use of m-Toluenesulfonyl chloride in the synthesis of these analogs contributes to the development of effective treatments for this condition.
4. Used in Treatment of Osteoporosis:
m-Toluenesulfonyl chloride is used as a reactant in the synthesis of 17β-HSD2 inhibitors. These inhibitors are essential in the development of drugs for the treatment of osteoporosis, a condition characterized by weak and brittle bones. By inhibiting the enzyme 17β-HSD2, these drugs can help maintain bone density and reduce the risk of fractures.
5. Used in Development of Histone Deactylase Inhibitors:
In the field of epigenetics, m-Toluenesulfonyl chloride is used as a reactant to synthesize isoindoline-5-propenehydroxamates. These compounds serve as histone deactylase inhibitors, which are important in the regulation of gene expression. By inhibiting histone deactylases, these compounds can potentially be used to treat various diseases, including cancer.

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

Upstream product

• 6399-00-4 S-(3-methylphenyl)-N,N-diethylcarbamate 
• 108-44-1 1-amino-3-methylbenzene 
• 108-40-7 toluene-3-thiol 
• 937-01-9 trimethyl(3-methylphenyl)stannane 
• 699-18-3 2-[(E)-2-nitroethenyl]furan 
• 2028-72-0 m-toluenediazonium chloride 
• 3728-44-7 3-(trimethylsilyl)toluene 
• 28987-79-3 m-tolylmagnesium bromide 
• 127-65-1 chloroamine-T 
• 68971-88-0 Tributyl-m-tolyl-stannane 
• 108-88-3 toluene 
• 591-17-3 meta-bromotoluene 
• 2004-90-2 Trimethyl-silyl-<3-methyl-benzol-sulfonat> 
• 617-97-0 m-toluenesulfonic acid 

Downstream Products

• 108-40-7 toluene-3-thiol 
• 1899-94-1 3-methylbenzenesulfonamide 
• 33065-46-2 3-(chloromethyl)benzenesulfonyl chloride 
• 670271-60-0 toluene-3-sulfonic acid p-toluidide 
• 116436-08-9 3-methyl-N-phenylbenzenesulfonamide 
• 53046-20-1 1-methyl-3-tosylbenzene 
• 5402-35-7 3-methyldiphenylsulphone 
• 93475-55-9 N-(5-butyl-[1,3,4]thiadiazol-2-yl)-toluene-3-sulfonamide 
• 66896-76-2 N-(2,4-Dichloro-benzoyl)-N-ethyl-3-methyl-benzenesulfonamide 
• 66897-37-8 N-Allyl-N-(2,4-dichloro-benzoyl)-3-methyl-benzenesulfonamide 
• 66897-36-7 N-Allyl-N-(2-chloro-benzoyl)-3-methyl-benzenesulfonamide 
• 82777-18-2 Toluene-3-sulfonic acid 3-p-tolylsulfanyl-propyl ester 
• 126865-07-4 methyl 3-methylbenzenesulfonate 
• 131700-56-6 C₂₀H₁₈O₆S₂ 

Relevant academic research and scientific papers

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.

New process for the production of arensulfonyl chloride from arensulfonic acid

The present invention refers to degradation of a fine chemicals functionalised in a synthetic process of intermediates to conversion of an important role new manufacturing method relates to a novel process of arylsulfonyl, arylsulfonyl chloride hour draw from previous techniques are nick biting opinion gun method for producing [...] the users determine a structure of basic presents at 70 degree or more time and an elongated reactant hot reaction of undesirable and uniform reaction conditions to improve power efficiency nick biting opinion gun a dilute bis (trichloromethyl) polycarbonate and a catalytic amount of potassium and phosphoric acid incorporated tetrahedral amorphous [...] triethylamine and tree hereinafter also 25 reacting under a condition of gently arylsulfonyl chloride characterized by high yield in the dye by providing new method, pesticide, medicine, as well as related industrial electronic materials of the field will hole is compressed by the reciprocal movement.

DABCO-bis (sulfur dioxide), DABSO, as a convenient source of sulfur dioxide for organic synthesis: Utility in sulfonamide and sulfamide preparation

The charge-transfer complex generated from the combination of DABCO and sulfur dioxide, DABSO, is a bench-stable colorless solid suitable for use in organic synthesis as a replacement for gaseous sulfur dioxide. The complex can be combined with Grignard reagents to form sulfinates, which can then be converted in situ to a series of sulfonamides. Alternatively, reaction with anilines and iodine leads to the formation of a series of sulfamides. Cheletropic addition between DABSO and 2,3-dimethylbutadiene provides the corresponding sulfolene.

Orally active aminopyridines as inhibitors of tetrameric fructose-1,6-bisphosphatase

A novel sulfonylureido pyridine series exemplified by compound 19 yielded potent inhibitors of FBPase showing significant glucose reduction and modest glycogen lowering in the acute db/db mouse model for Type-2 diabetes. Our inhibitors occupy the allosteric binding site and also extend into the dyad interface region of tetrameric FBPase.

(Arylsulfonyl)acetones and -acetonitriles: New activated methylenic building blocks for synthesis of 1,2,3-triazoles

β-Keto sulfones and b-nitrile sulfones were used as building blocks for 1,2,3-triazole synthesis in the Dimroth cyclization. It was shown, that sulfone reagents undergo base-catalyzed cyclization under mild conditions (at room temperature) to give 1,2,3-triazoles in moderate to excellent yields. This fact has confirmed the high nucleophilicity of sulfonylmethylenic compounds and allows new synthetic applications. Georg Thieme Verlag Stuttgart.

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.

Bispiperidines as antithrombotic agents

Novel compounds which are inhibitors of the binding of fibrinogen to the Gp IIb/IIIa platelet receptors, and which can be used therepeutically as antithrombotic agents

Elimination of substituted fluoren-9-ylmethyl benzenesulfonates: Hammett substituent effects at a mechanistic borderline

Rates of elimination of fourteen substituted fluoren-9-ylmethyl benzenesulfonates have been measured in methanolic sodium methoxide and 90% aqueous ethanolic solutions of triethylamine, trimethylamine and 4-methyl morpholine. For the sodium methoxide, a linear Hammett plot with ρ = 0.74, consistent with reaction by an E2 mechanism, is observed. For the amine bases the Hammett plots are curved, suggesting a transition from an E2 mechanism for electron-withdrawing substituents to an irreversible E1cB mechanism with a smaller value of ρ for electron-donating substituents. The evidence for a change of mechanism is weakened by systematic and random deviations of substituents from correlations which span small changes in reactivity (less than ten-fold), by a surprisingly large value of ρ = 2 implied for the concerted (E2) reaction and by the possible influence of negative hyperconjugation. Nevertheless, it is consistent with independent evidence that the borderline between concerted and stepwise mechanisms is associated with chemically distinguishable reaction paths, even though pronounced carbanion character (and probably a small extent of bond-breaking to the leaving group) ensures a degree of similarity of structure and sensitivity to substituents of their transition states.

Tin for Organic Synthesis, 13. A New and Regioselective Method for the Synthesis of Aromatic, Heteroaromatic, and Olefinic Sulfonamides by Electrophilic Destannylation

A mild and effective method for the preparation of aromatic and olefinic sulfonamides is described.The reaction of trialkylaryl- (4a-f), heteroaryl- (4g), and vinylic stannanes (4h) with sulfuryl chloride and secondary amines provides the corresponding sulfonamides in an ipso-specific manner. - Keywords: Electrophilic aromatic substitution ; Electrophilic vinylic substitution ; Trialkylstannanes, application of ; Sulfonamides, synthesis of ; Sulfodestannylation, application of