66107-36-6

Basic information

• Product Name: 2-CHLOROPHENYL TRIFLUOROMETHANESULFONATE
• Synonyms: 2-CHLOROPHENYL TRIFLUOROMETHANESULFONATE;Trifluoromethanesulfonic Acid 2-Chlorophenyl Ester 2-Chlorophenyl Triflate
• CAS NO: 66107-36-6
• Molecular Formula: C₇H₄ClF₃O₃S
• Molecular Weight: 260.62
• Mol File: 66107-36-6.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 120°C/33mmHg(lit.)
• Flash Point: 117.3oC
• Appearance: /
• Density: 1.6g/cm3
• Vapor Pressure: 0.0114mmHg at 25°C
• Refractive Index: 1.4560-1.4600
• CAS DataBase Reference: 2-CHLOROPHENYL TRIFLUOROMETHANESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROPHENYL TRIFLUOROMETHANESULFONATE(66107-36-6)
• EPA Substance Registry System: 2-CHLOROPHENYL TRIFLUOROMETHANESULFONATE(66107-36-6)

Safety Data

• Hazardous Substances Data: 66107-36-6(Hazardous Substances Data)

Usage

General Description

2-CHLOROPHENYL TRIFLUOROMETHANESULFONATE, also known as 2-Chlorobenzenetrifluoromethanesulfonate, is a chemical compound with the molecular formula C7H4ClF3O2S. It is a colorless to pale yellow liquid that is primarily used as a reagent in organic synthesis and as a coupling agent in peptide synthesis. This chemical is highly reactive and can undergo various chemical reactions, making it a versatile intermediate in the production of pharmaceuticals and agrochemicals. It is also used as a protecting group for alcohols in organic chemistry. However, caution should be exercised when handling this compound, as it is highly toxic and may cause irritation to the skin, eyes, and respiratory system.

InChI:InChI=1/C7H4ClF3O3S/c8-5-3-1-2-4-6(5)14-15(12,13)7(9,10)11/h1-4H

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 95-57-8 2-monochlorophenol 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 1493-13-6 trifluorormethanesulfonic acid 
• 1956-97-4 2-chlorobenzenediazonium tetrafluoroborate 

Downstream Products

• 141077-50-1 (S)-2-(2-chlorophenyl)-2,3-dihydrofuran 
• 141077-50-1 (R)-2-(2-chlorophenyl)-2,3-dihydrofuran 
• 141077-51-2 (R)-2-(2-chlorophenyl)-2,5-dihydrofuran 
• 141077-51-2 (S)-2-(2-chlorophenyl)-2,5-dihydrofuran 
• 95-57-8 2-monochlorophenol 
• 13029-08-8 2,2'-Dichlorobiphenyl 
• 349537-53-7 1-acetylamino-1-(2'-chlorophenyl)ethene 
• 18434-12-3 1,2-diphenyl-1H-indole 
• 15104-43-5 dimethyl (2-chlorophenyl)phosphonate 
• 149950-35-6 2'-chloro-[1,1'-biphenyl]-4-ol 
• 149950-34-5 2'-chlorobiphenyl-3-ol 
• 2051-60-7 2-chloro-1,1'-biphenyl 
• 15499-29-3 1-butyl-2-chlorobenzene 
• 10292-67-8 1-chloro-2-cyclopropylbenzene 

Relevant articles and documents

Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes

A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C–Br > C–Cl > C–OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki–Miyaura coupling reactions.

Modular Functionalization of Arenes in a Triply Selective Sequence: Rapid C(sp2) and C(sp3) Coupling of C?Br, C?OTf, and C?Cl Bonds Enabled by a Single Palladium(I) Dimer

Full control over multiple competing coupling sites would enable straightforward access to densely functionalized compound libraries. Historically, the site selection in Pd0-catalyzed functionalizations of poly(pseudo)halogenated arenes has been unpredictable, being dependent on the employed catalyst, the reaction conditions, and the substrate itself. Building on our previous report of C?Br-selective functionalization in the presence of C?OTf and C?Cl bonds, we herein complete the sequence and demonstrate the first general arylations and alkylations of C?OTf bonds (in I dimer. This allowed the realization of the first general and triply selective sequential C?C coupling (in 2D and 3D space) of C?Br followed by C?OTf and then C?Cl bonds.

Intermolecular mizoroki-heck reaction of aliphatic olefins with high selectivity for substitution at the internal position

New ligand for old reaction: The title reaction of aryltriflates with aliphatic olefins leads to substitution at the internal position with high selectivity. The ratio of the desired isomer (shown in the scheme) to the sum of all other isomers is generall