40630-63-5

Usage

Synthesis Reference(s)

Tetrahedron Letters, 16, p. 1429, 1975 DOI: 10.1016/S0040-4039(00)72160-5

Safety Profile

A mild skin and eye irritant.When heated to decomposition it emits toxic vapors ofSOx and Fí.

InChI:InChI=1/C8H17FO2S/c1-2-3-4-5-6-7-8-12(9,10)11/h2-8H2,1H3

Upstream product

• 111-88-6 Octanethiol 
• 1065131-41-0 n-octanesulfonyl hydrazide 
• 111-83-1 1-bromo-octane 
• 122-20-3 triisopropanolamine 
• 7795-95-1 octane-1-sulfonyl chloride 

Downstream Products

• 307-35-7 perfluorooctyl sulfofluorure 
• 375-72-4 Nonafluorobutanesulfonyl fluoride 
• 42036-73-7 1-(non-1-enyl)benzene 
• 42036-73-7 1-((E)-non-1-enyl)benzene 
• 111735-48-9 (Z)-1-(non-1-enyl)benzene 
• 17763-87-0 Phloroglucin-tris(perfluoroctansulfonat) 
• 17763-74-5 Perfluoroctansulfonsaeure-3-m-tolylester 
• 17763-86-9 Perfluoroctansulfonsaeure-m-phenylendiester 
• 559-05-7 N-phenyl perfluorooctanesulfonamide 
• 17763-82-5 Perfluoroctansulfonsaeure-(2,4-diphenoxyphenyl)ester 
• 17763-85-8 Perfluoroctansulfonsaeure-o-phenylendiester 
• 17763-94-9 2,2'-Dihydroxy-4,4'-bis(perfluoroctylsulfonyloxy)benzophenon 
• 17763-72-3 Perfluoroctansulfonsaeure-4-methoxycarbonyl-phenylester 
• 17763-77-8 Perfluoroctansulfonsaeure-4-benzyloxyphenylester 

Relevant academic research and scientific papers

Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride

Sulfonyl fluorides are valuable synthetic motifs for a variety of applications, among which sulfur(VI) fluoride exchange-based "click chemistry" is currently the most prominent. Consequently, the development of novel and efficient synthetic methods to access these functional groups is of great interest. Herein, we report a mild and environmentally benign electrochemical approach to prepare sulfonyl fluorides using thiols or disulfides, as widely available starting materials, in combination with KF, as an inexpensive, abundant and safe fluoride source. No additional oxidants nor additional catalysts are required and, due to mild reaction conditions, the reaction displays a broad substrate scope, including a variety of alkyl, benzyl, aryl and heteroaryl thiols or disulfides.

One-pot fluorosulfurylation of Grignard reagents using sulfuryl fluoride

Herein, we report a new method for the one-pot syntheses of sulfonyl fluorides. Addition of an alkyl, aryl, or heteroaryl Grignard to a solution of sulfuryl fluoride at ambient temperature affords the desired sulfonyl fluorides in 18-78% yield. Furthermore, this method is applicable for in situ sequential reactions, whereby the Grignard reagent can be converted to the corresponding diarylsulfone, sulfonate ester, or sulfonamide in a one-pot process.

A fluoride compound of preparation method

The invention relates to a preparation method of a sulfuryl fluoride compound. A sulfonyl hydrazide compound and a fluoride reagent serve as reaction raw materials. The preparation method includes the steps that a, the sulfonyl hydrazide compound with the structure (I) and the fluoride reagent are dispersed in a solvent, wherein the structure (I) is shown in the specification; b; a mixture obtained from the step a is stirred and heated to obtain the sulfuryl fluoride compound with the structure (II), wherein the structure (II) is shown in the specification (II). Compared with existing related technologies in the chemical synthesis field, the method of preparing sulfuryl fluoride from sulfonyl hydrazide is achieved for the first time. In the method, no catalyst needs to be added, reaction conditions are moderate, good compatibility can be achieved for water and air, and large-scale production is easy to achieve. The experimental result indicates that the yield of the obtained sulfuryl fluoride compound can reach up to 98%.

Catalyst-free radical fluorination of sulfonyl hydrazides in water

The first catalyst-free fluorination of sulfonyl hydrazides for the synthesis of sulfonyl fluorides has been developed via a free-radical pathway. This protocol presents a broad substrate scope and does not require any metal catalyst and additive. All these transformations proceed smoothly in water under mild conditions, which enables a straightforward, practical and environmentally benign fluorination for S-F bond formation.

Process for preparing sulfonic acid fluorides

Sulfonic acid fluorides are prepared by reacting sulfonic acid halides with inorganic fluorides in an organic-aqueous phase. The reaction is carried out in the presence of catalytic amounts of an amine or an onium salt.