17763-67-6

Basic information

• Product Name: PHENYL TRIFLUOROMETHANESULFONATE
• Synonyms: PHENYL TRIFLUOROMETHANESULFONATE;PHENYL TRIFLATE;Phenol triflate;Phenol trifluoromethanesulfonate;Trifluoromethanesulfonic acid phenyl ester;Trifluoromethylsulfonyloxybenzene;Trifluoromethanesulfonic Acid Phenyl Ester Phenyl Triflate;Phenyl trifluoromethanesulfonate 98%
• CAS NO: 17763-67-6
• Molecular Formula: C₇H₅F₃O₃S
• Molecular Weight: 226.17
• Mol File: 17763-67-6.mol
• Article Data: 61

Chemical Properties

• Boiling Point: 99-100 °C60 mm Hg(lit.)
• Flash Point: 160 °F
• Appearance: /
• Density: 1.396 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0862mmHg at 25°C
• Refractive Index: n20/D 1.435(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: PHENYL TRIFLUOROMETHANESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYL TRIFLUOROMETHANESULFONATE(17763-67-6)
• EPA Substance Registry System: PHENYL TRIFLUOROMETHANESULFONATE(17763-67-6)

Safety Data

• Hazard Codes: T
• Statements: 36/37/38-34-24/25
• Safety Statements: 26-36-45-36/37/39
• RIDADR: UN 2927 6.1/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 17763-67-6(Hazardous Substances Data)

Usage

Chemical Properties

Colorless Liquid.

Uses

Phenyl trifluoromethanesulfonate (phenyl triflate) may be used in the following studies:As an arylating agent for the asymmetric α-arylation of ketones catalyzed by Pd(dba)2 and difluorphos.As a reactant in the one pot synthesis of carbazoles by palladium-catalyzed N-arylation of anilines with phenyl triflate followed by oxidative coupling.Synthesis of N-(2,6-diarylbenzoyl)anilines by diarylation of benzanilides with phenyl triflate in the presence of palladium-based catalyst.As an arylating agent in the synthesis of (R)-2-phenyl-2,3-dihydrofuran by the arylation of 2,3-dihydrofuran.

Preparation

Synthesis of Phenyl trifluoromethanesulfonate: The reaction of phenol (1.00 g, 10.6 mmol) with triflic anhydride as outlined in the general procedure provided phenyl trifluoromethanesulfonate as colorless oil (0.73 g, 30%).1H NMR (400 MHz, CDCl3) δ 7.50 – 7.42 (m, 2H), 7.41 – 7.36 (m, 1H), 7.32 – 7.24 (m, 2H).

General Description

Phenyl trifluoromethanesulfonate (phenyl triflate) is an aryl fluorosulphonate. It has been synthesized by the reaction of phenol with fluorosulphonic anhydride.

InChI:InChI=1/C7H5F3O3S/c8-7(9,10)14(11,12)13-6-4-2-1-3-5-6/h1-5H

Upstream product

• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 108-95-2 phenol 
• 109586-39-2 4-iodophenyl trifluoromethanesulfonate 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 139-02-6 sodium phenoxide 
• 1493-13-6 trifluorormethanesulfonic acid 
• 603-33-8 triphenylbismuthane 
• 2926-30-9 sodium triflate 
• 98-80-6 phenylboronic acid 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 122-79-2 Phenyl acetate 
• 150-19-6 O-methylresorcine 
• 673-32-5 1-Phenylprop-1-yne 

Downstream Products

• 36586-17-1 (E)-(2-butoxyethenyl)benzene 
• 56750-84-6 (1-butoxyethenyl)benzene 
• 98-86-2 acetophenone 
• 937-58-6 (3E)-4-phenyl-3-buten-1-ol 
• 3174-83-2 3-phenylbut-3-en-1-ol 
• 145372-92-5 4-phenyl-4H-1,3-dioxin 
• 92-67-1 4-phenylalanine 
• 90-41-5 2-phenylaniline 
• 6590-79-0 N,N-diethyl-[1,1'-biphenyl]-2-amine 
• 5412-43-1 4-(N,N-diethylamino)biphenyl 
• 103-69-5 N-ethyl-N-phenylamine 
• 71-43-2 benzene 
• 104-53-0 3-phenyl-propionaldehyde 
• 190788-58-0 4,4,5,5-tetramethyl-2-(4-methylsulfanylphenyl)-[1,3,2]-dioxaborolane 

Relevant articles and documents

Ni-Catalyzed Cross-Electrophile Coupling of Aryl Triflates with Thiocarbonates via C-O/C-O Bond Cleavage

A nickel-catalyzed reductive coupling of aryl triflates with thiocarbonates is reported here. Both electron-rich and -deficient aryl C(sp2)-O electrophiles as well as a class of O-tBu S-alkyl thiocarbonates are compatible with the optimized reaction conditions, as evidenced by 49 examples. The reaction also proceeds with good chemoselective cleavage of the C-O bond with regard to thioesters. This work broadens the scope of nickel-catalyzed reductive cross-electrophile coupling reactions.

Nickel-Catalyzed Arylation/Alkenylation of tert-Cyclobutanols with Aryl/Alkenyl Triflates via a C - C Bond Cleavage

Herein, we first present a nickel-catalyzed arylation and alkenylation of tert-cyclobutanols with aryl/alkenyl triflates via a C-C bond cleavage. An array of γ-substituted ketones was obtained in moderate-to-good yields, thus featuring earth-abundant nick

Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts

Herein we present a Bi-catalyzed cross-coupling of arylboronic acids with perfluoroalkyl sulfonate salts based on a Bi(III)/Bi(V) redox cycle. An electron-deficient sulfone ligand proved to be key for the successful implementation of this protocol, which allows the unusual construction of C(sp2)-O bonds using commercially available NaOTf and KONf as coupling partners. Preliminary mechanistic studies as well as theoretical investigations reveal the intermediacy of a highly electrophilic Bi(V) species, which rapidly eliminates phenyl triflate.