368-85-4

Basic information

• Product Name: 4-FLUOROBENZENESULFONYL FLUORIDE
• Synonyms: 4-FLUOROBENZENESULFONYL FLUORIDE
• CAS NO: 368-85-4
• Molecular Formula: C₆H₄F₂O₂S
• Molecular Weight: 178.16
• Product Categories: Miscellaneous
• Mol File: 368-85-4.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 198.7°Cat760mmHg
• Flash Point: 74°C
• Appearance: /
• Density: 1.432g/cm³
• Vapor Pressure: 0.501mmHg at 25°C
• Refractive Index: 1.487
• CAS DataBase Reference: 4-FLUOROBENZENESULFONYL FLUORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-FLUOROBENZENESULFONYL FLUORIDE(368-85-4)
• EPA Substance Registry System: 4-FLUOROBENZENESULFONYL FLUORIDE(368-85-4)

Safety Data

• Hazardous Substances Data: 368-85-4(Hazardous Substances Data)

Usage

General Description

4-Fluorobenzenesulfonyl fluoride, also known as FBFSF, is a chemical compound with the molecular formula C6H4F2O2S. It is a colorless, odorless solid that is soluble in organic solvents. FBFSF is a fluorosulfonyl fluoride compound that is commonly used as a reagent in organic synthesis, particularly in the preparation of sulfonamides and other pharmaceutical intermediates. It is a highly reactive compound, known for its ability to form stable covalent bonds with nucleophiles, making it useful in the synthesis of complex organic molecules. However, FBFSF is also a potent irritant and must be handled with care and appropriate protective equipment.

InChI:InChI=1/C6H4F2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H

Upstream product

• 74321-38-3 p-Fluorbenzolsulfinsaeurefluorid 
• 349-88-2 4-Fluorobenzenesulfonyl chloride 
• 2266-41-3 4-fluorobenzenesulfonylhydrazide 
• 352-13-6 4-flourophenylmagnesium bromide 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 1765-93-1 4-fluoroboronic acid 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 371-42-6 4-Fluorothiophenol 
• 2070902-77-9 trifluoromethyl 4-fluorobenzene-1-sulfonate 
• 2993-24-0 4-(pentafluorosulfanyl)aniline 
• 2557-81-5 pentafluorosulfanylbenzene 
• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 
• 1605274-62-1 4-(pentafluoro-λ⁶-sulfaneyl)benzenediazonium tetrafluoroborate 
• 824-80-6 sodium 4-fluorobenzenesulfinate 

Downstream Products

• 349-88-2 4-Fluorobenzenesulfonyl chloride 
• 683203-79-4 2-(4-fluoro-benzenesulfonyl)-indole-1-carboxylic acid tert-butyl ester 
• 324-74-3 4-fluoro-biphenyl 
• 312-31-2 4-(phenylsulfonyl)fluorobenzene 
• 13656-61-6 2-methylphenyl phenyl p-fluorobenzenesulfonate 
• 2924-72-3 ethyl 4-fluorobenzenesulfonate 

Relevant articles and documents

Discovery and Safety Profiling of a Potent Preclinical Candidate, (4-[4-[[(3 R)-3-(Hydroxycarbamoyl)-8-azaspiro[4.5]decan-3-yl]sulfonyl]phenoxy]- N -methylbenzamide) (CM-352), for the Prevention and Treatment of Hemorrhage

Discovery of potent and safe therapeutics that improve upon currently available antifibrinolytics, e.g., tranexamic acid (TXA, 1) and aprotinin, has been challenging. Matrix metalloproteinases (MMPs) participate in thrombus dissolution. Then we designed a

Visible-Light-Mediated Synthesis of Sulfonyl Fluorides from Arylazo Sulfones

Sulfonyl fluorides are useful motifs for a wide range of applications in organic synthesis including sulfur (VI) fluoride exchange-based “click chemistry.” Herein, a visible-light-mediated synthesis of sulfonyl fluorides from arylazo sulfones is described. In the present study, K2S2O5 and N-fluorobenzenesulfonimide (NFSI) were used as the sulfonyl source and fluorinating agent, respectively, for visible-light-mediated fluorosulfonylation of arylazo sulfones to prepare various sulfonyl fluorides in 60–85% yield. This protocol is a synthetic approach to provide useful sulfonyl fluoride structures at room temperature. (Figure presented.).

Metal-Free Visible-Light Synthesis of Arylsulfonyl Fluorides: Scope and Mechanism

The first metal-free procedure for the synthesis of arylsulfonyl fluorides is reported. Under organo-photoredox conditions, aryl diazonium salts react with a readily available SO2 source (DABSO) to afford the desired product through simple nucleophilic fluorination. The reaction tolerates the presence of both electron-rich and -poor aryls and demonstrated a broad functional group tolerance. To shed the light on the reaction mechanism, several experimental techniques were combined, including fluorescence, NMR, and EPR spectroscopy as well as DFT calculations.

Arenesulfonyl Fluoride Synthesis via Copper-free Sandmeyer-type Fluorosulfonylation of Arenediazonium Salts

The limited availability of highly valuable arenesulfonyl fluorides seriously hinders their further application in many research fields including medicinal chemistry and chemical biological, organic synthesis, polymer preparation, etc. We report herein a mild and efficient copper-free Sandmeyer-type fluorosulfonylation reaction of various arenediazonium salts to prepare valuable arenesulfonyl fluorides using K2S2O5 as both a reductant and a practical sulfonyl source in combination with N-fluorobenzenesulfonimide as an effective fluorine source. This methodology provides an attractive route to diverse important arenesulfonyl fluorides given the overall practicality and scope.