128373-13-7

Basic information

• Product Name: 1H-Indol-5-yl trifluoromethanesulfonate
• Synonyms: 1H-Indol-5-yl trifluoromethanesulfonate
• CAS NO: 128373-13-7
• Molecular Formula: C₉H₆F₃NO₃S
• Molecular Weight: 265.21
• Mol File: 128373-13-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 370.6°C at 760 mmHg
• Flash Point: 178°C
• Appearance: /
• Density: 1.624g/cm³
• Vapor Pressure: 2.33E-05mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1H-Indol-5-yl trifluoromethanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indol-5-yl trifluoromethanesulfonate(128373-13-7)
• EPA Substance Registry System: 1H-Indol-5-yl trifluoromethanesulfonate(128373-13-7)

Safety Data

• Hazardous Substances Data: 128373-13-7(Hazardous Substances Data)

Usage

General Description

1H-Indol-5-yl trifluoromethanesulfonate, also known as 5-Trifluoromethylsulfonylindole, is a chemical compound with the molecular formula C10H7F3NO3S. It is a trifluoromethanesulfonate ester of 5-indole, and it is commonly used as a reagent in organic synthesis for the introduction of the trifluoromethanesulfonate group onto various substrates. 1H-Indol-5-yl trifluoromethanesulfonate is an important building block for the synthesis of pharmaceuticals, agrochemicals, and materials. Its unique properties and versatile reactivity make it a valuable tool for synthetic chemists in the development of new compounds with potential biological and industrial applications.

InChI:InChI=1/C9H6F3NO3S/c10-9(11,12)17(14,15)16-7-1-2-8-6(5-7)3-4-13-8/h1-5,13H

Upstream product

• 1953-54-4 indol-5-ol 
• 456-64-4 phenyl trifluoromethanesulfonamide 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 1493-13-6 trifluorormethanesulfonic acid 
• 358-23-6 trifluoromethylsulfonic anhydride 

Downstream Products

• 10075-50-0 5-bromo-1H-indole 
• 66616-72-6 5-phenyl-1H-indole 

Relevant articles and documents

SuFEx-enabled, chemoselective synthesis of triflates, triflamides and triflimidates

Sulfur(vi) Fluoride Exchange (SuFEx) chemistry has emerged as a next-generation click reaction, designed to assemble functional molecules quickly and modularly. Here, we report the ex situ generation of trifluoromethanesulfonyl fluoride (CF3SO2F) gas in a two chamber system, and its use as a new SuFEx handle to efficiently synthesize triflates and triflamides. This broadly tolerated protocol lends itself to peptide modification or to telescoping into coupling reactions. Moreover, redesigning the SVI-F connector with a SO → SNR replacement furnished the analogous triflimidoyl fluorides as SuFEx electrophiles, which were engaged in the synthesis of rarely reported triflimidate esters. Notably, experiments showed H2O to be the key towards achieving chemoselective trifluoromethanesulfonation of phenols vs. amine groups, a phenomenon best explained - using ab initio metadynamics simulations - by a hydrogen bonded termolecular transition state for the CF3SO2F triflylation of amines. This journal is

Selective arylation and vinylation at the α position of vinylarenes

In intermolecular Heck reactions of styrene and vinylarenes, the aryl and vinyl groups routinely insert at the β position. However, selective insertion at the α position has been very rare. Herein, we provide a missing piece in the palette of Heck reaction, which gave >20:1 α selectivity. The key to our success is a new ferrocene 1,1′-bisphosphane (dnpf) that carries 1-naphthyl groups. Our mechanistic studies revealed that the high α selectivity is partly attributable to the steric effect of dnpf. The rigid and bulky 1-naphthyl groups of dnpf sterically disfavor β insertion. What the Heck! In intermolecular Heck reactions, insertion at the β position of aromatic olefins is very common, but reversal of the selectivity for selective α insertion has been a longstanding problem. A general method to couple aryl and vinyl triflates with aromatic olefins in >20:1 α selectivity is presented. The key to this successful approach is a new ferrocene bisphosphane with naphthyl groups on the phosphorus atom (see scheme; OTf=triflate). Copyright

Preparation and Palladium-Catalyzed Cross-Coupling of Aryl Triethylammonium Bis(catechol) Silicates with Aryl Triflates

Pentavalent aryl and heteroaryl bis(catechol) silicates undergo palladium-catalyzed cross-coupling with aryl and heteroaryl triflates in the presence of a fluoride source in excellent yields. These solid, air-stable bis(catechol) silicates are prepared from a high-yielding displacement reaction between catechol and an aryl siloxane in the presence of an amine base. The cross-coupling reaction is tolerant of a wide range of electron-donating and electron-withdrawing groups. Several examples of di-ortho-substituted triflates are successfully coupled with these reagents.