20621-29-8

Basic information

• Product Name: TRIFLUOROMETHYL SULFINYL CHLORIDE
• Synonyms: TRIFLUOROMETHYL SULFINYL CHLORIDE;TrifluoroMethanesulfinyl chloride;Methanesulfinylchloride, 1,1,1-trifluoro-
• CAS NO: 20621-29-8
• Molecular Formula: CClF₃OS
• Molecular Weight: 152.52
• Mol File: 20621-29-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 149.4±35.0 °C(Predicted)
• Appearance: /
• Density: 1.852±0.06 g/cm3(Predicted)
• CAS DataBase Reference: TRIFLUOROMETHYL SULFINYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIFLUOROMETHYL SULFINYL CHLORIDE(20621-29-8)
• EPA Substance Registry System: TRIFLUOROMETHYL SULFINYL CHLORIDE(20621-29-8)

Safety Data

• Hazardous Substances Data: 20621-29-8(Hazardous Substances Data)

Usage

Description

TRIFLUOROMETHYL SULFINYL CHLORIDE, also known as the reagent Togni reagent, is a chemical compound with the formula CF3SCl. It is a highly reactive and versatile compound used in organic synthesis for the introduction of the trifluoromethylthio group into organic molecules. Its ability to facilitate transition metal-catalyzed trifluoromethylation reactions makes it a valuable tool in modern synthetic chemistry. However, due to its reactivity and potential hazards, it should be handled with caution.

Uses

Used in Pharmaceutical Industry:
TRIFLUOROMETHYL SULFINYL CHLORIDE is used as a reagent for the synthesis of trifluoromethylthio-containing compounds, which have numerous applications in the pharmaceutical industry. The introduction of the trifluoromethylthio group into organic molecules can enhance the biological activity and pharmacological properties of these compounds, making them more effective in treating various diseases.
Used in Agrochemical Industry:
TRIFLUOROMETHYL SULFINYL CHLORIDE is used as a reagent in the agrochemical industry for the synthesis of trifluoromethylthio-containing agrochemicals. These compounds can improve the effectiveness of pesticides and herbicides, leading to better crop protection and increased agricultural productivity.
Used in Organic Synthesis:
TRIFLUOROMETHYL SULFINYL CHLORIDE is used as a reagent in organic synthesis for the efficient preparation of a wide range of trifluoromethylthio-containing compounds. Its versatility allows for the synthesis of various complex organic molecules with potential applications in different fields, such as materials science, pharmaceuticals, and agrochemicals.
Used in Transition Metal-Catalyzed Trifluoromethylation Reactions:
TRIFLUOROMETHYL SULFINYL CHLORIDE is used as a valuable tool in modern synthetic chemistry for facilitating transition metal-catalyzed trifluoromethylation reactions. This allows for the selective introduction of the trifluoromethyl group into organic molecules, which can significantly improve their properties and applications in various industries.

Upstream product

• 812-12-4 trifluoromethanesulfinyl fluoride 
• 2926-29-6 Langlois reagent 
• 51735-87-6 N-(trichlorophosphoranylidene)trifluoromethanesulfinamide 

Downstream Products

• 51735-89-8 trifluoromethanesulfinyl isocyanate 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 169046-52-0 5-(N-trifluoromethylsulfinyl)-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole 
• 120068-37-3 fipronil 
• 627546-03-6 (R)-4-Phenyl-3-((S)-trifluoromethanesulfinyl)-oxazolidin-2-one 

Relevant articles and documents

Transition-Metal-Free Electrophilic Fluoroalkanesulfinylation of Electron-Rich (Het)Arenes with Fluoroalkyl Heteroaryl Sulfones via C(Het)?S and S=O Bond Cleavage

A novel Ph2P(O)Cl-mediated direct fluoroalkanesulfinylation of electron-rich (het)arenes using fluoroalkyl heteroaryl sulfones as the RfSO source (Rf=C4F9, CF2Cl, CF2Br, and CF2COOEt) was developed. This is the first example where 2-HetSO2Rf performs as the RfSO synthon in organic synthesis via both C(Het)?S and S=O bond cleavage. (Figure presented.).

Preparation process of trifluoromethyl sulfinyl chloride

The invention provides a preparation process of trifluoromethyl sulfinyl chloride. The preparation process comprises the steps as follows: 1) a synthesis kettle is taken, and thionyl chloride is added; 2) thionyl chloride is heated until reflux and cooled to 0-5 DEG C, and sodium trifluoromethanesulfinate is fed; 3) the temperature is increased to 15-20 DEG C, distillation is performed, the steam is turned off and the temperature is reduced to 10 DEG C or lower when the temperature reaches 90-100 DEG C, and water is added to clean a distillation kettle; 4) the material is distilled into a rectifying still, the rectifying still starts to heat up, front cut fractions are collected after reflux for 3-5 hours, whether the material in the reflux pipe is transparent is observed when the temperature reaches 40-45 DEG C, and a finished product of trifluoromethyl sulfinyl chloride is collected if the material is transparent, and reflux is continued if the material is not transparent; 5) the finished product is stopped from being collected when the temperature reaches 45-50 DEG C, reflux is continued, and the finished product of trifluoromethyl sulfinyl chloride continues to be collected after the reflux temperature is reduced. The process is simple to operate, is green and has no pollutant discharge during preparation, is energy-saving, consumption-reducing and good in economic benefit, an adopted solvent is recyclable, obtained trifluoromethyl sulfinyl chloride has high purity and yield, and the production cost can be effectively reduced.

REAGENT AND PROCESS WHICH ARE USEFUL FOR GRAFTING A SUBSTITUTED DIFLUOROMETHYL GROUP ONTO A COMPOUND CONTAINING AT LEAST ONE ELECTROPHILIC FUNCTION

The invention relates to a nucleophilic reagent which is useful for grafting a substituted difluoromethyl group onto a compound containing at least one electrophilic function, or for the synthesis of oxysulphide-containing and fluorine-containing organic derivatives, wherein said reagent comprises: a) a fluorocarboxylic acid of formula Ew—CF2—COOH where Ew represents an electron-withdrawing atom or group, at least partially salified with an organic or inorganic cation, and b) a polar aprotic solvent; and in that the content of releasable protons carried by its various components, including their impurities, is at most equal to half the initial molar concentration of the said fluorocarboxylic acid. A synthetic process uses this reagent by heating in order to graft a substituted difluoromethyl group onto various compounds.