107658-27-5

Basic information

• Product Name: 3-PYRIDYL TRIFLUOROMETHANESULFONATE
• Synonyms: 3-PYRIDYL TRIFLUOROMETHANESULFONATE;1,1,1-Trifluoro-Methanesulfonic Acid 3-Pyridinyl Ester;3-Pyridyl Triflate;3-TrifluoroMethanesulfonyloxypyridine;Trifluoromethanesulfonic Acid 3-Pyridyl Ester 3-Pyridyl Triflate
• CAS NO: 107658-27-5
• Molecular Formula: C₆H₄F₃NO₃S
• Molecular Weight: 227.1610696
• Product Categories: Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides
• Mol File: 107658-27-5.mol

Chemical Properties

• Appearance: /
• Refractive Index: 1.4360 to 1.4400
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: 3-PYRIDYL TRIFLUOROMETHANESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PYRIDYL TRIFLUOROMETHANESULFONATE(107658-27-5)
• EPA Substance Registry System: 3-PYRIDYL TRIFLUOROMETHANESULFONATE(107658-27-5)

Safety Data

• Hazardous Substances Data: 107658-27-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Pyridyl Trifluoromethanesulfonate is used as a reagent in organic synthesis for its ability to facilitate a range of chemical reactions. Its light yellow oil form allows for easy handling and integration into various processes, making it a versatile compound for use in the creation of new molecules and compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Pyridyl Trifluoromethanesulfonate is used as a key intermediate in the synthesis of various drugs and pharmaceutical compounds. Its unique chemical properties enable the development of new drugs with improved efficacy and reduced side effects, contributing to the advancement of medical treatments.
Used in Chemical Research:
3-Pyridyl Trifluoromethanesulfonate is also employed in chemical research as a tool to study and understand the behavior of different chemical reactions. Its use in research helps scientists gain insights into the mechanisms of various chemical processes, leading to the development of new methodologies and techniques in the field of chemistry.
Used in Material Science:
In the field of material science, 3-Pyridyl Trifluoromethanesulfonate is used as a component in the development of new materials with specific properties. Its unique chemical characteristics allow for the creation of materials with enhanced performance, such as improved stability, reactivity, or selectivity, which can be applied in various industries, including electronics, energy, and environmental protection.

Upstream product

• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 100-67-4 potassium phenolate 
• 139-02-6 sodium phenoxide 
• 109-00-2 3-HYDROXYPYRIDINE 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 462-08-8 pyridin-3-ylamine 
• 1493-13-6 trifluorormethanesulfonic acid 

Downstream Products

• 124643-40-9 o-[2-(pyridin-3-yl)ethynyl]aniline 
• 53340-10-6 diethyl pyridin-3-ylphosphonate 
• 1008-88-4 3-phenylpyridine 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 104114-99-0 (pyridin-3-yl)diphenylphosphine 
• 92118-22-4 3-isonicotine 
• 15432-24-3 2-(pyridin-3-yl)-indole 
• 539-32-2 3-butylpyridine 
• 1198091-36-9 1-(3'-pyridyl)-1-(3'',4'',5''-trimethoxyphenyl)ethylene 
• 372-47-4 3-Fluoropyridine 
• 5424-19-1 3-Benzoylpyridine 
• 678140-94-8 diphenyl(pyridine-3-yl)phosphine oxide 
• 614-18-6 3-pyridinecarboxylic acid ethyl ester 
• 510703-88-5 N-(furan-2-ylmethyl)pyridin-3-amine 

Relevant articles and documents

A soluble polymer-supported triflating reagent: a high-throughput synthetic approach to aryl and enol triflates.

[reaction: see text] The high-yielding synthesis and application of the first example of a polymer-supported reagent for the preparation of trifluoromethanesulfonates (triflates) is described. This new reagent efficiently triflates aryl alcohols and lithi

Aryl triflates and [11C]/(13C)carbon monoxide in the synthesis of 11C-/13C-amides

Palladium(0)-mediated carbonylation reactions using aryl triflates, amines, and a low concentration of [11C]carbon monoxide were used in the syntheses of 13 11C-labeled amides. Lithium bromide was used as an additive to facilitate the reaction. The 11C-labeled products were obtained with decay-corrected radiochemical yields in the range of 2-63%. The radiochemical purity of the final products exceeded 98%. As an example, a reaction starting with 1.79 GBq [11C]carbon monoxide gave 0.38 GBq of LC-purified N-isopropyl-4-nitro-[11C]benzamide within 27 min from the start of the carbonylation reaction (54% decay-corrected radiochemical yield). The specific radioactivity of this compound was 191 GBq/μmol, 35 min after the end of a 10 μAh bombardment. N-Benzyliso-quinoline-1-(13C)carboxamide was prepared and analyzed by NMR for confirmation of the labeling position. The triflates 16, 20, 21, and 22 were synthesized from the corresponding alcohols and trifluoromethanesulfonic anhydride. The reference compounds 30a and 30b were prepared from the corresponding carboxylic acids and benzylamine. The other nine reference compounds 32a to 32i were synthesized from the respective acid chlorides and amines. The presented report shows that the sometimes more easily obtainable aryl triflates can be a useful alternative to the commonly used aryl halides in palladium(0)-mediated synthesis of 11C/13C-amides.

Palladium Catalysed Alkoxycarbonylation of Phenols to Benzoate Esters

The methoxycarbonylation of aryl trifluoromethanesulphonates with CO and aliphatic alcohols is catalysed by Pd(OAc)2-1,3-bis(diphenylphosphino)propane in high yield at 70 deg C and ambient CO pressure.

Palladium-Catalyzed Reductive Carbonylation of (Hetero) Aryl Halides and Triflates Using Cobalt Carbonyl as CO Source

An efficient protocol for the reductive carbonylation of (hetero) aryl halides and triflates under CO gas-free conditions using Pd/Co2(CO)8 and triethylsilane has been developed. The mild reaction conditions, enhanced chemoselectivity and, easy access to heterocyclic and vinyl carboxaldehydes highlights its importance in organic synthesis.

Solvent-free ruthenium-catalysed triflate coupling as a convenient method for selective azole-o-C-H monoarylation

Metal-catalysed ortho-directed C-H functionalization usually faces selectivity issues in the competition between mono- and disubstitution processes. We report herein the ruthenium-catalysed N-directed C-H monoarylation of arylpyrazoles with a selectivity

Directed ortho Metalation (D o M)-Linked Corriu-Kumada, Negishi, and Suzuki-Miyaura Cross-Coupling Protocols: A Comparative Study

A systematic study of the widely used, titled name reaction transition-metal-catalyzed cross-coupling reactions with attention to context with the directed ortho metalation (D o M) is reported. In general, the Suzuki-Miyaura and Negishi protocols show gre

Pd-Catalyzed Conjunctive Cross-Coupling between Grignard-Derived Boron “Ate” Complexes and C(sp2) Halides or Triflates: NaOTf as a Grignard Activator and Halide Scavenger

Catalytic enantioselective conjunctive cross-couplings that employ Grignard reagents are shown to furnish an array of nonracemic chiral organoboronic esters in an efficient and highly selective fashion. The utility of sodium triflate in facilitating this reaction is two-fold: it enables “ate” complex formation and overcomes catalytic inhibition by halide ions.

A Nickel-Catalyzed Carbonyl-Heck Reaction

The use of transition-metal catalysis to enable the coupling of readily available organic molecules has greatly enhanced the ability of chemists to access complex chemical structures. In this work, an intermolecular coupling reaction that unites organotriflates and aldehydes is presented. A unique catalyst system is identified to enable this reaction, featuring a Ni0 precatalyst, a tridentate Triphos ligand, and a bulky amine base. This transformation provides access to a variety of ketone-containing products without the selectivity- and reactivity-related challenges associated with more traditional Friedel–Crafts reactions. A Heck-type mechanism is postulated, wherein the π bond of the aldehyde takes the role of the olefin in the insertion/elimination steps.

A Novel Convenient Synthesis of Pyridinyl and Quinolinyl Triflates and Tosylates via One-Pot Diazotization of Aminopyridines and Aminoquinolines in Solution

The first effective and simple method for the direct one-pot transformation of 2-, 3-, and 4-aminopyridines, 2,6-diaminopyridines, and 2-aminoquinoline into the corresponding pyridinyl and quinolinyl trifluoromethanesulfonates and tosylates in solvents was developed. The procedure involves diazotization of the heterocyclic amines with sodium nitrite in mixed hexane-DMSO or hexane-DMF solutions in the presence of trifluoromethanesulfonic acid or p-toluenesulfonic acid.

Nickel-catalyzed phosphorylation of aryl triflates with P([Formula presented] compounds

A nickel-catalyzed phosphorylation of aryl triflates with P([Formula presented] compounds is disclosed. This reaction can proceed smoothly under a mild reaction condition, producing the corresponding aryl phosphorus compounds in good to high yields.