7795-95-1

Usage

Uses

Used in Chemical Synthesis Industry:
1-Octanesulfonyl chloride is used as a reagent for the preparation of 1-alkyl-3-methylimidazolium alkylsulfonates, which are a class of ionic liquids. These ionic liquids are known for their unique properties, such as low melting points, high thermal stability, and excellent solvation capabilities. They are widely used in various applications, including catalysis, electrochemistry, and as solvents for a range of chemical reactions.
Used in Catalysts:
1-Octanesulfonyl chloride can be used as a catalyst in certain chemical reactions due to its ability to form stable intermediates and facilitate the reaction process. Its reactivity and stability make it a promising candidate for use in various catalytic applications.
Used in Electrochemistry:
In the field of electrochemistry, 1-Octanesulfonyl chloride can be utilized in the development of ionic liquid-based electrolytes for batteries and supercapacitors. The ionic liquids derived from 1-OCTANESULFONYL CHLORIDE can improve the performance and stability of these energy storage devices.
Used in Solvent Applications:
Due to its solvation properties, 1-Octanesulfonyl chloride can be used as a solvent in various chemical processes. Its ability to dissolve a wide range of compounds makes it suitable for use in industries that require efficient and effective solvents for their processes.

InChI:InChI=1/C8H17ClO2S/c1-2-3-4-5-6-7-8-12(9,10)11/h2-8H2,1H3

Upstream product

• 111-88-6 Octanethiol 
• 5324-84-5 sodium octylsulfonate 
• 4270-03-5 2-n-octylisothiourea hydrobromide 
• 3944-72-7 1-octanesulfonic acid 
• 822-27-5 dioctyl disulfide 
• 111-83-1 1-bromo-octane 
• 19942-78-0 octyl thiocyanate 
• 85293-39-6 octyl benzyl sulfide 
• 69422-58-8 S,S-dioctyl dithiocarbonate 

Downstream Products

• 5455-54-9 ethyl octanesulfonate 
• 307-34-6 Perfluorooctane 
• 307-35-7 perfluorooctyl sulfofluorure 
• 65501-71-5 1-octanesulfonamide 
• 5454-98-8 N-phenyloctane-1-sulfonamide 
• 5455-74-3 N,N-dibenzyloctane-1-sulfonamide 
• 38920-21-7 Octane-1-sulfonic acid [4-(1-amino-4-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yloxy)-phenyl]-amide 
• 122833-59-4 Octane-1-sulfonic acid [(1R,2R)-2-(octane-1-sulfonylamino)-cyclohexyl]-amide 
• 88413-13-2 N-<3-(methylamino)-4-nitrophenyl>octanesulfonamide 
• 111-85-3 n-chlorooctane 
• 629-27-6 1-Iodooctane 
• 3944-72-7 1-octanesulfonic acid 

Relevant academic research and scientific papers

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.

Synthesis of Sultams and Cyclic N-Sulfonyl Ketimines via Iron-Catalyzed Intramolecular Aliphatic C-H Amidation

Cyclic sulfonamides (sultams) play a unique role in drug discovery and synthetic chemistry. A direct synthesis of sultams by an intramolecular C(sp3)-H amidation reaction using an iron complex in situ derived from Fe(ClO4)2 and aminopyridine ligand is reported. This strategy features a readily available catalyst and tolerates a broad variety of substrates as demonstrated by 22 examples (up to 89% yield). A one-pot iron-catalyzed amidation/oxidation procedure for the synthesis of cyclic N-sulfonyl ketimines is also realized with up to 92% yield (eight examples). The synthetic utility of the method is validated by a gram-scale reaction and derivatization of the products to ring-fused sultams.

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.

Tert -Butyl Hypochlorite Mediated Oxidative Chlorination of S -Alkylisothiourea Salts: Synthesis of Sulfonyl Chlorides

Under neutral conditions, a variety of S-alkylisothiourea salts were smoothly converted into the corresponding sulfonyl chlorides through tert-butyl chlorite mediated oxidative chlorination in good to excellent yields after simple purification. In addition to the environmental and procedural advantages of this method, the neutral conditions potentially make it applicable to substrates that bear acid-sensitive functional groups. For example, the Cbz-protected 2-aminoethanesulfonyl chloride could be synthesized in moderate to good yields under the current neutral conditions, and the acid-sensitive Cbz-protecting group was not affected.

Clean and economic synthesis of alkanesulfonyl chlorides from S-alkyl isothiourea salts via bleach oxidative chlorosulfonation

A simple procedure for clean and economic synthesis of alkanesulfonyl chlorides via bleach-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is disclosed. This procedure is environment- and worker-friendly with the advantages of readily accessible materials and reagents, simple and safe operations, easy purification without chromatography, and affords high yields of up to 99%.

Synthesis of sulfonyl chlorides and sulfonic acids in SDS micelles

H2O2/POCl3 is found to be a reactive reagent system that can be used in sodium dodecyl sulfate (SDS) micellar solution in aqueous media for the direct oxidative chlorination of thiol and di-sulfide derivatives to give the desired sulfonyl chlorides. The oxidation of thiols and disulfides to sulfonic acids with this system is also reported. In most cases, these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity. Georg Thieme Verlag Stuttgart · New York.

Synthesis of sulfonyl chlorides and thiosulfonates from H2O 2-TiCl4

A new method is described for the oxidative chlorination of thiols to sulfonyl chlorides using titanium tetrachloride in combination with the oxidant hydrogen peroxide. Direct conversion of thiols into their corresponding thiosulfonates is also reported. Good to excellent yields, short reaction times, high efficiencies, cost-effectiveness, and, facile isolation of the desired products make the present methodology a practical alternative.

TAPC-promoted synthesis of sulfonyl chlorides from sulfonic acids

A novel and efficient method is described for the preparation of sulfonyl chlorides from sulfonic acids using TAPC as chlorinating agent. Mild reaction conditions, shorter reaction times, high efficiencies, cost-effectiveness, and facile isolation of the desired products make the present methodology a practical alternative and will provide a valuable synthetic tool for various pharmaceutical applications. Georg Thieme Verlag Stuttgart · New York.

A novel, practical synthesis of sulfonyl chlorides from thiol and disulfide derivatives

Hydrogen peroxide, in the presence of zirconium tetrachloride, is a very efficient reagent for the direct oxidative conversion of thiol and disulfide derivatives into the corresponding sulfonyl chlorides with high purity through oxidative chlorination. Excellent yields, very short reaction times, mild reaction conditions, and the avoidance of harsh reagents are the main advantages of this method.

Direct conversion of thiols to sulfonyl chlorides and sulfonamides

(Chemical Equation Presented) H2O2 in combination with SOCl2 proved to be a highly reactive reagent for the direct oxidative conversion of thiol derivatives to the corresponding sulfonyl chlorides with high purity through oxidative chlorination. Upon reaction with amines, the corresponding sulfonamides were obtained in excellent yields and in very short reaction times.