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

General Description

TRIFLUOROMETHYL SULFINYL CHLORIDE, also known as the reagent Togni reagent, is a chemical compound with the formula CF3SCl. It is commonly used as a reagent in organic synthesis for the introduction of the trifluoromethylthio group into organic molecules. It is a highly reactive and versatile compound that allows for the efficient preparation of a wide range of trifluoromethylthio-containing compounds, which have numerous applications in the pharmaceutical and agrochemical industries. TRIFLUOROMETHYL SULFINYL CHLORIDE is known for its ability to facilitate transition metal-catalyzed trifluoromethylation reactions, making it a valuable tool in modern synthetic chemistry. However, it should be handled with caution due to its reactivity and potential hazards.

Upstream product

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

Downstream Products

• 51735-82-1 Trifluoro-methanesulfinic acid methylamide 
• 655226-88-3 4-fluorophenyl trifluoromethanesulfinate 
• 169046-52-0 5-(N-trifluoromethylsulfinyl)-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole 
• 120068-37-3 fipronil 
• 372-64-5 Bis(trifluoromethyl)disulfid 
• 358-15-6 Trifluoro-methanethiosulfonic acid S-trifluoromethyl ester 
• 421-17-0 Trifluoromethylsulfenyl chloride 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 14177-25-4 thionyl chlorofluoride 
• 75-73-0 carbon tetrafluoride 
• 353-50-4 Carbonyl fluoride 
• 75-72-9 chlorotrifluoromethane 
• 7719-09-7 thionyl chloride 
• 7782-50-5 chlorine 

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.