368-42-3

Basic information

• Product Name: cyclohexanesulfonyl fluoride
• Synonyms: Cyclohexanesulfonyl fluoride
• CAS NO: 368-42-3
• Molecular Formula: C₆H₁₁FO₂S
• Molecular Weight: 166.2137
• Mol File: 368-42-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 237.1°C at 760 mmHg
• Flash Point: 97.2°C
• Density: 1.23g/cm³
• Vapor Pressure: 0.0703mmHg at 25°C
• Refractive Index: 1.455
• CAS DataBase Reference: cyclohexanesulfonyl fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: cyclohexanesulfonyl fluoride(368-42-3)
• EPA Substance Registry System: cyclohexanesulfonyl fluoride(368-42-3)

Safety Data

• Hazardous Substances Data: 368-42-3(Hazardous Substances Data)

Upstream product

• 126812-30-4 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate 
• 931-50-0 cyclohexylmagnesium bromide 
• 4837-39-2 S-cyclohexyl cyclohexane-1-sulfonothioate 
• 2550-40-5 1,2-dicyclohexyl disulfide 
• 1569-69-3 Cyclohexanethiol 
• 4837-38-1 cyclohexanesulfonyl chloride 

Relevant articles and documents

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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.

Oxidation of disulfides with electrophilic halogenating reagents: Concise methods for preparation of thiosulfonates and sulfonyl halides

The reaction of aromatic or benzylic disulfides with 2.5 equiv of Selectfluor in acetonitrile/water (10:1) at room temperature efficiently produced the corresponding thiosulfonates. Conversely, the reaction of disulfides with 6.5 equiv of Selectfluor or thiosulfonates with 4.5 equiv of Selectfluor in refluxing acetonitrile/water (10:1) provided sulfonyl fluorides in high yields. Accufluor and FP-T300 are also effective in preparing sulfonyl fluorides from disulfides under the similar reaction conditions. Sulfonyl chlorides or sulfonyl bromides were effectively obtained from the reaction of disulfides with 6 equiv of either N-chlorosuccinimide or N-bromosuccinimide in acetonitrile/water (10:1) at room temperature. Some other electrophilic chlorinating or brominating reagents are also able to be used instead of N-chlorosuccinimide or N-bromosuccinimide for the syntheses of sulfonyl halides from disulfides. These reactions of disulfides with electrophilic halogenating reagents are convenient methods to prepare thiosulfonates and sulfonyl halides.