943-08-8

Usage

Uses

Used in Pharmaceutical Industry:
2-(Difluoromethylthio)benzothiazole is used as a key intermediate in the synthesis of various pharmaceuticals due to its unique chemical structure and biological activity, contributing to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(difluoromethylthio)benzothiazole is utilized as a building block for the creation of pesticides and antifungal agents, leveraging its biological properties to protect crops and enhance agricultural productivity.
Used in Material Science:
2-(Difluoromethylthio)benzothiazole is employed in material science for its potential applications in the development of organic light-emitting diodes (OLEDs) and organic semiconductors, where its chemical properties can improve device performance and efficiency.

Upstream product

• 1097192-99-8 N-toluylsulfonyl S-difluoromethyl S-phenyl sulfoximine 
• 149-30-4 2-Mercaptobenzothiazole 
• 65094-22-6 diethyl (bromodifluoromethyl)phosphonate 
• 150542-06-6 α,α,α-iodinefluoroacetophenone 
• 1885-46-7 trifluoromethanesulfonic acid difluoromethyl ether 
• 137-07-5 2-amino-benzenethiol 
• 275818-95-6 sodium difluoromethanesulfinate 
• 136-95-8 2-amino-benzthiazole 
• 115262-01-6 [bromo(difluoro)methyl]-trimethyl-silane 
• 1895-39-2 sodium chlorodifluoroacetate 
• 75-45-6 Chlorodifluoromethane 
• 2492-26-4 sodium 2-mercaptobenzothiazole 

Downstream Products

• 186204-66-0 2-(difluoromethanesulfonyl)-1,3-benzothiazole 
• 1286740-21-3 C₁₇H₁₅F₂NO₂S₂ 

Relevant academic research and scientific papers

Regio- and chemoselectivity in S- and O- difluoromethylation reactions using diethyl (bromodifluoromethyl)phosphonate

The effective difluoromethylations of various S- and O- based- nucleophiles, presenting a wide range of pKa values, using diethyl(bromodifluoromethyl) phosphonate (1) under basic conditions is described. These reactions, which rely on the quantitative generation of difluorocarbene formed through the hydrolysis of 1, were found to be effective only once the starting materials had pKa values of less than ca. 11. Importantly, in cases in which the substrates held two or three nucleophilic centers this feature was successfully implemented to achieve a high chemo- or regioselective difluoromethylation of the center exhibiting the lowest pKa value and the highest polarizability.

Study on the mild, rapid and selective difluorocarbene-mediated triclassification of iododifluoroacetophenone with secondary amines and tree model for product classification

Difluorocarbene is a very active and widely used intermediate in organic synthesis. In this work, a room temperature difluorocarbene-mediated triclassification reaction of iododifluoroacetophenone (2) and secondary amines with mild condition, short reaction time (only 10 min) and high selectivity had been studied, which produced one of the following three substances: N-CF2H derivatives (up to 87% yield), formamides (82–89% yield) or the recycled starting secondary amines. This phenomenon was related to the structural stability of the corresponding products. If unstable, it would be hydrolyzed to formamides first, and then further hydrolyzed to starting amines. Based on the geometric structure of the raw materials, the corresponding prediction tree model was established, which provided guidance for the further application of difluoromethylation of Vemurafenib (1ee) and AZD9291 (1ff).

PRMT5 INHIBITORS

The present invention provides a compound of Formula (I) and the pharmaceutically acceptable salts, esters, and prodrugs thereof, which are PRMT5 inhibitors. Also provided are methods of making compounds of Formula I, pharmaceutical compositions comprising compounds of Formula I, and methods of using these compounds to treat cancer, sickle cell, and hereditary persistence of foetal hemoglobin (HPFH) mutations.

FLUORINE-CONTAINING COMPOUNDS FOR USE AS NUCLEOPHILIC REAGENTS FOR TRANSFERRING FUNCTIONAL GROUPS ONTO HIGH VALUE ORGANIC COMPOUNDS

The present invention relates to a compound of general formulae (I) and their use as reagents

Deoxygenative tri- And difluoromethylthiolation of carboxylic acids with benzothiazolium reagents

Deoxygenative syntheses of fluorinated thioesters directly from carboxylic acids have been developed employing benzothiazolium reagents. The process using BT-SCF3 represents an attractive approach toward these SCF3containing compounds that avoids the use of metal ?SCF3 salts or preactivated acyl electrophiles. Moreover, the in situ activation of BT-SCF2H allows for an unprecedented nucleophilic difluoromethylthiolation reaction. DFT calculations support a mechanistic scenario involving a four-membered transition state where acyl substitution occurs without the formation of an unstable free ?SCF2H anion.

Difluoromethylation of Phenols and Thiophenols with the S-(Difluo-romethyl)sulfonium Salt: Reaction, Scope, and Mechanistic Study

A facile and practical approach for the difluoromethylation of phenols and thiophenols was described. Making use of the recently developed bench-stable S-(difluoromethyl)sulfonium salt as the difluorocarbene precursor, a wide variety of diversely functionalized phenols and thiophenols were readily converted to their corresponding aryl difluoromethyl ethers in good to excellent yields in the presence of lithium hydroxide. Chemoselectivity of various O,S-nucleophiles toward difluorocarbene was systematically studied, suggesting the reactivity order ArS- > RS-, ArO- > ROH > RO-, ArSH, ArOH, RSH.

Visible-Light- and Oxygen-Promoted Direct Csp2-H Radical Difluoromethylation of Coumarins and Antifungal Activities

An efficient general method using a clean and transition-metal-free photochemical strategy for the direct Csp2-H radical difluoromethylation of coumarins with HCF2SO2Na was developed. The visible-light-promoted strategy proceeds with 5 mol % Eosin Y under mild reaction conditions and showed excellent functional group compatibility. The control experiments illustrated that O2? - participated in this process and plays an important role in the reactions. Moreover, the representative products exhibited excellent antifungal activities in vitro. It was noted that the EC50 value of compound 3a was determined to be as low as 1.5463 μg/mL against Rhizoctorzia solani, which was better than Boscalid (EC50 = 2.9767 μg/mL).

CF2-containing 2-oxazoline ketone compounds and preparation method thereof

The invention provides a method for mildly and efficiently compounding a series of CF2-containing 2-oxazoline ketone compounds under a photocatalysis condition by actively combining difluoroalkylationreaction with carbon dioxide. The method provided by th

Radical Difluororomethylation of Thiols with Difluoromethylphosphonium Triflate under Photoredox Catalysis

A convenient, visible light-induced radical difluoromethylation of aryl-, heteroaryl-, and alkylthiols with difluoromethyltriphenylphosphonium triflate was developed to afford various difluoromethyl thioethers in moderate to excellent yields. The key reaction features include the use of a readily available CF2H radical source, mild reaction conditions, and excellent chemoselective thiol-difluoromethylation.

Sodium difluoromethanesulfinate—A difluoromethylating agent toward protonated heterocyclic bases

Free radical difluoromethylation of protonated heteroaromatic bases was accomplished using sodium difluoromethanesulfinate in combination with tert-butyl hydroperoxide in a two-phase system (methylene chloride–water) at room temperature. The difluoromethylation products of methyl pyridine-4-carboxylate, pyridine-4-carbonitrile, and 2-amino-1,3,4-thiadiazole were isolated on a preparative scale.