186204-66-0

Usage

Uses

Used in Organic Synthesis:
2-(difluoromethanesulfonyl)-1,3-benzothiazole is utilized as a key intermediate in organic synthesis for the creation of various biologically active compounds. Its sulfonyl fluoride group allows for versatile reactions, making it a valuable component in the development of new organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-(difluoromethanesulfonyl)-1,3-benzothiazole serves as a promising scaffold for the design and synthesis of novel drug candidates. Its unique structure and reactivity enable the exploration of its potential in treating various diseases and conditions, contributing to the advancement of medicinal chemistry and drug development.
Used in Medicinal Chemistry:
2-(difluoromethanesulfonyl)-1,3-benzothiazole is employed as a structural element in the field of medicinal chemistry to enhance the properties of drug molecules. Its incorporation can improve pharmacokinetics, such as solubility, stability, and bioavailability, as well as modulate the activity of drug candidates, leading to more effective therapeutic agents.

Upstream product

• 910803-66-6 ethyl α-(1,3-benzothiazol-2-ylsulfonyl)-α-fluoroacetate 
• 477889-77-3 ethyl 2-(benzo[d]thiazol-2-ylsulfonyl)-2,2-difluoroacetate 
• 1241899-81-9 2-(benzo[d]thiazol-2-ylsulfonyl)-1-(4-bromophenyl)-2,2-difluoroethanone 
• 943-08-8 2-[(difluoromethyl)sulfanyl]-1,3-benzothiazole 
• 2492-26-4 sodium 2-mercaptobenzothiazole 
• 149-30-4 2-Mercaptobenzothiazole 
• 75-45-6 Chlorodifluoromethane 

Downstream Products

• 1286740-21-3 C₁₇H₁₅F₂NO₂S₂ 
• 152878-34-7 2,6-anhydro-1-deoxy-1,1-difluoro-3,4,5,7-tetrakis-O-benzyl-D-gluco-hept-1-enitol 
• 275818-95-6 sodium difluoromethanesulfinate 
• 7144-49-2 2-methanesulfonylbenzothiazole 
• 1610500-99-6 6-(difluoromethyl)-2,4-difluorophenanthridine 
• 1610501-04-6 6-(difluoromethyl)-8-phenylphenanthridine 

Relevant academic research and scientific papers

Late-Stage 18F-Difluoromethyl Labeling of N-Heteroaromatics with High Molar Activity for PET Imaging

Despite a growing interest in CHF2 in medicinal chemistry, there is a lack of efficient methods for the insertion of CHF18F into druglike compounds. Herein described is a photoredox flow reaction for 18F-difluoromethylation of N-heteroaromatics that are widely used in medicinal chemistry. Following the two-step synthesis for a new 18F-difluoromethylation reagent, the photoredox reaction is completed within two minutes and proceeds by C?H activation, circumventing the need for pre-functionalization of the substrate. The method is operationally simple and affords straightforward access to radiolabeled N-heteroaromatics with high molar activity suitable for biological in vivo studies and clinical application.

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).

Electrochemical reduction of fluoroalkyl sulfones for radical fluoroalkylation of alkenes

Radical fluoroalkylation of alkenes has been developed by electrochemical reduction of fluoroalkyl sulfones. A series of electron-deficient alkenes readily undergo hydrofluoroalkylation in good to excellent yields. This chemistry represents the first example of electrochemical generation of fluoroalkyl radicals from sulfones, which are used for practical radical fluoroalkylation of organic compounds.

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.

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

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.

Metal-Free Difluoromethylthiolation, Trifluoromethylthiolation, and Perfluoroalkylthiolation with Sodium Difluoromethane- sulfinate, Sodium Trifluoromethanesulfinate or Sodium Perfluoro- alkanesulfinate

A method for direct difluoromethylthiolation of Ar?H bonds is introduced. The stable and easy-to-handle HCF2SO2Na is reduced with (EtO)2P(O)H in the presence of TMSCl to generate HCF2S+ for the regioselective difluoromethylthiolation of aromatic compounds including indoles, pyrroles, and activated benzenes. This method is also applicable for the trifluoromethylthiolation with CF3SO2Na and the perfluoroalkylthiolation with RfSO2Na of arenes and heteroarenes. Reaction mechanisms associated with the metal-free electrophilic fluoroalkylthiolation reactions are also discussed. (Figure presented.).

Radical Fluoroalkylation of Isocyanides with Fluorinated Sulfones by Visible-Light Photoredox Catalysis

The radical fluoroalkylation of isocyanides with fluorinated sulfones is enabled by visible-light photoredox catalysis. A wide range of readily available mono-, di-, and trifluoromethyl heteroaryl sulfones can thus be used as efficient radical fluoroalkylation reagents under mild conditions. This method not only describes a new synthetic application of fluorinated sulfones, but also provides a new route to fluoroalkyl radicals.

Modified Julia olefination on sugar-derived lactones: Synthesis of difluoro exo-glycals

We report the preparation of difluoro-exo-glycals by gem-difluoroolefination of benzylated sugar-derived lactones using a modified Julia reaction. The addition is highly stereo-selective, and the Smiles-rearrangement-elimination sequence can be carried out under microwave irradiation.

From difluoromethyl 2-pyridyl sulfone to difluorinated sulfonates: A protocol for nucleophilic difluoro(sulfonato)methylation

An efficient method for the synthesis of alkyl α,α- difluorosulfonates has been developed. The selection of the 2-pyridyl group as the aryl substitute on the sulfone is critically important for the success of this transformation (see scheme). The synthetic application of fluorinated sulfones is extended and a unique solution is provided for a long-standing challenge in nucleophilic difluoro(sulfonato)methylation reactions. Copyright