188975-30-6

Basic information

• Product Name: 3,6-DIHYDRO-2H-PYRAN-4-YL TRIFLUORO-METHANESULFONATE
• Synonyms: 3,6-DIHYDRO-2H-PYRAN-4-YL TRIFLUORO-METHANESULFONATE;Methanesulfonic acid, 1,1,1-trifluoro-, 3,6-dihydro-2H-pyran-4-yl ester;Trifluoromethanesulfonic acid 3,6-dihydro-2H-pyran-4-yl ester
• CAS NO: 188975-30-6
• Molecular Formula: C₆H₇F₃O₄S
• Molecular Weight: 232.18
• Mol File: 188975-30-6.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 261.2°C at 760 mmHg
• Flash Point: 111.8°C
• Appearance: /
• Density: 1.53g/cm³
• Vapor Pressure: 0.019mmHg at 25°C
• Refractive Index: 1.443
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 3,6-DIHYDRO-2H-PYRAN-4-YL TRIFLUORO-METHANESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-DIHYDRO-2H-PYRAN-4-YL TRIFLUORO-METHANESULFONATE(188975-30-6)
• EPA Substance Registry System: 3,6-DIHYDRO-2H-PYRAN-4-YL TRIFLUORO-METHANESULFONATE(188975-30-6)

Safety Data

• Hazardous Substances Data: 188975-30-6(Hazardous Substances Data)

Usage

General Description

3,6-Dihydro-2H-pyran-4-yl trifluoro-methanesulfonate is a chemical compound with the molecular formula C7H9F3O4S. It is a synthetic reagent often used in organic synthesis as a mild and selective Lewis acid catalyst. 3,6-DIHYDRO-2H-PYRAN-4-YL TRIFLUORO-METHANESULFONATE is known for its ability to efficiently promote a variety of chemical reactions, including allylation, acylation, and aldol condensation. It is commonly used in the pharmaceutical and agrochemical industries as a versatile building block for the synthesis of complex organic molecules. Additionally, 3,6-Dihydro-2H-pyran-4-yl trifluoro-methanesulfonate is also used in the production of flavors and fragrances, as well as in the synthesis of natural products and biologically active compounds. Overall, this compound plays a crucial role as a catalyst and intermediate in the production of a wide range of organic compounds.

InChI:InChI=1/C6H7F3O4S/c7-6(8,9)14(10,11)13-5-1-3-12-4-2-5/h1H,2-4H2

Upstream product

• 29943-42-8 Tetrahydro-4H-pyran-4-one 
• 107-83-5 2-Methylpentane 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 456-64-4 phenyl trifluoromethanesulfonamide 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 84302-42-1 2,3-dihydro-4H-pyran-4-one 
• 145100-51-2 N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide 

Downstream Products

• 803687-56-1 4-(3,6-dihydro-2H-pyran-4-yl)-3-fluoroaniline 
• 287944-16-5 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran 
• 1173199-90-0 (S)-2-(3,4-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1173199-91-1 (1R)-1-[(2R)-5,6-dihydro-2H-pyran-2-yl]-3-phenyl-propan-1-ol 
• 1173199-92-2 3-benzyloxy-(1R)-1-[(2R)-5,6-Dihydro-2H-pyran-2-yl]-propan-1-ol 
• 1173199-93-3 (1R)-[(2R)-5,6-dihydro-2H-pyran-2-yl]-phenyl-methanol 
• 3174-81-0 4-phenyl-5,6-dihydro-2H-pyran 

Relevant articles and documents

Alkenylation and Arylation of Peptides via Ni-Catalyzed Reductive Coupling of α- C-Tosyl Peptides with Csp2Triflates/Halides

A Ni-catalyzed reductive cross-coupling between α-C-tosyl peptides and Csp2 triflates/halides has been developed. This protocol enables the formation of various unnatural di- and tripeptides containing vinyl and aryl side chains, and it expands the applications of Ni-catalyzed reductive cross-coupling in late-stage diversification of peptides.

Three-Component Difunctionalization of Cyclohexenyl Triflates: Direct Access to Versatile Cyclohexenes via Cyclohexynes

Difunctionalization of strained cyclic alkynes presents a powerful strategy to build richly functionalized cyclic alkenes in an expedient fashion. Herein we disclose an efficient and flexible approach to achieve carbohalogenation, dicarbofunctionalization, aminohalogenation and aminocarbonation of readily available cyclohexenyl triflates. We have demonstrated the novel use of zincate base/nucleophile system for effective formation of key cyclohexyne intermediates and selective addition of various carbon and nitrogen nucleophiles. Importantly, leveraging the resulting organozincates enables the incorporation of a broad range of electrophilic partners to deliver structurally diverse cyclohexene motifs. The importance and utility of this method is also exemplified by the modularity of this approach and the ease in which even highly complex polycyclic scaffolds can be accessed in one step.

Nickel-Catalyzed Decarboxylative Alkenylation of Anhydrides with Vinyl Triflates or Halides

Decarboxylative cross-coupling of aliphatic acid anhydrides with vinyl triflates or halides was accomplished via nickel catalysis. This methodology works well with a broad array of substrates and features abundant functional group tolerance. Notably, our approach addresses the issue of safe and environmental installation of methyl or ethyl group into molecular scaffolds. The method possesses high chemoselectivity toward alkyl groups when aliphatic/aromatic mixed anhydrides are involved. Furthermore, diverse ketones could be modified with our strategy.