405-18-5

Basic information

• Product Name: (E)-2-phenylethenesulfonyl fluoride
• Synonyms: Ethenesulfonyl fluoride, 2-phenyl-
• CAS NO: 405-18-5
• Molecular Formula: C₈H₇FO₂S
• Molecular Weight: 186.2034
• Mol File: 405-18-5.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 287.8°C at 760 mmHg
• Flash Point: 127.9°C
• Density: 1.326g/cm³
• Vapor Pressure: 0.0042mmHg at 25°C
• Refractive Index: 1.552
• CAS DataBase Reference: (E)-2-phenylethenesulfonyl fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-phenylethenesulfonyl fluoride(405-18-5)
• EPA Substance Registry System: (E)-2-phenylethenesulfonyl fluoride(405-18-5)

Safety Data

• Hazardous Substances Data: 405-18-5(Hazardous Substances Data)

Usage

Description

(E)-2-phenylethenesulfonyl fluoride, also known as styrene sulfonyl fluoride, is a chemical compound that serves as a reagent in organic synthesis. It is characterized by its colorless liquid form with a pungent odor and is highly reactive due to the presence of a sulfonyl fluoride group. (E)-2-phenylethenesulfonyl fluoride is known for its versatility in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.

Uses

Used in Pharmaceutical Synthesis:
(E)-2-phenylethenesulfonyl fluoride is used as a sulfonating agent for the synthesis of pharmaceuticals. Its reactivity allows for the creation of a wide range of drug molecules, making it a valuable tool in the development of new medications.
Used in Agrochemical Production:
In the agrochemical industry, (E)-2-phenylethenesulfonyl fluoride is utilized as a sulfonating agent in the production of various compounds. Its ability to react with different substrates contributes to the development of effective agrochemicals for agricultural applications.
Used in Organic Synthesis:
(E)-2-phenylethenesulfonyl fluoride is employed as a precursor for the production of other organosulfur compounds. Its unique reactivity enables the synthesis of a variety of organosulfur molecules, which are important in various chemical and industrial processes.
Used in Fluorination Reactions:
(E)-2-phenylethenesulfonyl fluoride has been studied for its potential use as a fluorinating agent in organic reactions. Its ability to introduce fluorine atoms into organic molecules can lead to the development of new compounds with unique properties and applications.

Upstream product

• 677-25-8 ethylenesulfonyl fluoride 
• 98-80-6 phenylboronic acid 
• 591-50-4 iodobenzene 
• 4091-26-3 β-styrenesulfonyl chloride 
• 100-42-5 styrene 
• 52147-97-4 trans 2-phenylethenesulfonyl chloride 
• 292638-85-8 acrylic acid methyl ester 
• 107-13-1 acrylonitrile 
• 1629-58-9 4-penten-3-one 
• 2680-03-7 N,N-Dimethylacrylamide 
• 5535-48-8 PVS 
• 71-43-2 benzene 

Relevant articles and documents

N-Heterocyclic Carbene Catalyzed Synthesis of δ-Sultones via α,β-Unsaturated Sulfonyl Azolium Intermediates

A limited array of reactive intermediates have enabled a wealth of discoveries in N-heterocyclic carbene organocatalysis. In this study, the viability of α,β-unsaturated sulfonyl azoliums as double electrophiles in new reactions is examined. Specifically,

Preparation method of sulfuryl fluoride product

At present, reported reagents which can be used as compounds for direct sulfonylfluorination are mostly sulfonyl fluoride cation (FSO) reagents, but fluorosulfonyl free radical (FSO2) fluorosulfonylation reagents are not reported yet. The invention discloses application of sulfonyl fluoride chloride (SO2FCl) as a fluorosulfonyl free radical source for the first time, and fluorosulfonyl free radicals (FSO2) can be stably generated under various conditions, so a series of carbon-carbon double bonds or carbon-carbon triple bonds can be subjected to addition to prepare polysubstituted vinylsulfonyl fluoride compounds. The free radical fluorosulfonylation method is expected to be widely applied to the fields of organic synthesis, drug development, high polymer materials and the like.

Converting (E)-(Hetero)arylethanesulfonyl Fluorides to (Z)-(Hetero)arylethanesulfonyl Fluorides Under Light Irradiation

The construction of (Z)-(hetero)arylethenesulfonyl fluorides was achieved utilizing Iridium photoredox catalysis under UV-light irradiation. This protocol provided a diverse range of (Z)-(hetero)arylethenesulfonyl fluorides in moderate to good yields under mild conditions without external additives. The late-stage transformation of the (Z)-(hetero)arylethenesulfonyl fluorides comparing with their E-configuration counterparts was also studied.