17763-67-6 Usage
Description
Phenyl trifluoromethanesulfonate, also known as phenyl triflate, is an aryl fluorosulfonate that has been synthesized by the reaction of phenol with fluorosulfonic anhydride. It is a colorless liquid and is widely used in various chemical reactions and synthesis processes due to its reactivity and stability.
Uses
Used in Chemical Synthesis:
Phenyl trifluoromethanesulfonate is used as an arylating agent for the asymmetric α-arylation of ketones, catalyzed by Pd(dba)2 and difluorphos. This application is significant in the synthesis of various organic compounds and pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, phenyl triflate is used as a reactant in the one-pot synthesis of carbazoles. This process involves palladium-catalyzed N-arylation of anilines with phenyl triflate followed by oxidative coupling, which is crucial for the development of new drugs and therapeutic agents.
Used in Organic Chemistry Research:
Phenyl triflate is utilized in the synthesis of N-(2,6-diarylbenzoyl)anilines by diarylation of benzanilides with phenyl triflate in the presence of a palladium-based catalyst. This application is essential for the development of novel organic compounds with potential applications in various fields.
Used in Synthesis of Chiral Compounds:
Phenyl trifluoromethanesulfonate is employed as an arylating agent in the synthesis of (R)-2-phenyl-2,3-dihydrofuran by the arylation of 2,3-dihydrofuran. This process is vital for the production of chiral compounds, which are crucial in the pharmaceutical and chemical industries for their unique properties and applications.
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).
Check Digit Verification of cas no
The CAS Registry Mumber 17763-67-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,7,7,6 and 3 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 17763-67:
(7*1)+(6*7)+(5*7)+(4*6)+(3*3)+(2*6)+(1*7)=136
136 % 10 = 6
So 17763-67-6 is a valid CAS Registry Number.
InChI:InChI=1/C7H5F3O3S/c8-7(9,10)14(11,12)13-6-4-2-1-3-5-6/h1-5H
17763-67-6Relevant articles and documents
Effenberger,Mack
, p. 3947 (1970)
Ni-Catalyzed Cross-Electrophile Coupling of Aryl Triflates with Thiocarbonates via C-O/C-O Bond Cleavage
Zhu, Zhaodong,Gong, Yuxin,Tong, Weiqi,Xue, Weichao,Gong, Hegui
supporting information, p. 2158 - 2163 (2021/04/05)
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
Wang, Zhen,Hu, Yuanyuan,Jin, Hongwei,Liu, Yunkui,Zhou, Bingwei
, p. 466 - 474 (2020/12/22)
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
Palladium-Catalyzed Synthesis of N, N-Dimethylanilines via Buchwald-Hartwig Amination of (Hetero)aryl Triflates
Pospech, Jola,Taeufer, Tobias
, p. 7097 - 7111 (2020/06/27)
This work delineates the synthesis of N,N-dimethylaniline derivatives from dimethylamines and aryl triflates. The palladium-catalyzed C-N bond formation proceeds in excellent yields, using an unsophisticated catalytic system, a mild base, and triflates as electrophiles, which are readily available from inexpensive phenols. N,N-Dimethylanilines are multifunctional reaction partners and represent useful but underutilized building blocks in organic synthesis.
