80522-42-5 Usage
Description
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE is a highly reactive silylating agent and Lewis acid used in various organic synthesis reactions. It is a colorless oil with a boiling point of 83-87°C/1.7 mmHg and a density of 1.173 g cm-3. Its chemical properties include a clear light brown to orange-brown liquid.
Uses
Used in Organic Synthesis:
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE is used as a reagent for the introduction of triisopropylsilyl (TIPS) group in organic synthesis. It is involved in the synthesis of 2-substituted benzothiopyran-4-ones and silyloxy acetylenes.
Used as a Protecting Group:
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE is used as a protecting group in organic synthesis, especially for the protection of primary amines.
Used in Takahashi Taxol Total Synthesis:
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE plays an important role in Takahashi Taxol total synthesis or for chemical glycosylation reactions.
Used in Silylation of Alcohols:
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE is used for converting primary and secondary alcohols to the corresponding triisopropylsilyl ethers.
Used in Formation of Enol Silyl Ethers:
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE is used for converting ketones and lactones into their enol silyl ethers.
Used in Protection of Terminal Alkynes:
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE is used for the protection of terminal alkynes.
Used in Promoting Conjugate Addition of Alkynylzinc Compounds:
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE is used for promoting conjugate addition of alkynylzinc compounds to α,β-enones.
Used in Preparation of (Triisopropylsilyl)diazomethane:
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE participates in the preparation of (triisopropylsilyl)diazomethane.
Used in Triisopropylsiloxycarbonyl (Tsoc) and BIPSOP Protecting Groups for Amines:
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE is used in the formation of Triisopropylsiloxycarbonyl (Tsoc) and BIPSOP protecting groups for amines.
Used in TIPS Protection for Oxazoles/Regioselective Trapping of C-2 Oxazole Anions:
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE is used for TIPS protection for oxazoles and regioselective trapping of C-2 oxazole anions.
Used in Benzannulation Using Triisopropylsilyl Vinyl Ketenes:
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE is used in benzannulation using triisopropylsilyl vinyl ketenes.
Used in Cyclization of 1-Silyloxy-1,5-diynes:
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE is used in the cyclization of 1-silyloxy-1,5-diynes.
Used in Desymmetrization of Tartaric Acid Esters:
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE is used in the desymmetrization of tartaric acid esters.
Preparation
To 38.2 g (0.242 mol) of triisopropylsilane
at 0°C under argon is added 23.8 mL (0.266 mol) of trifluoromethanesulfonic
acid dropwise. The solution is stirred at
22°C for 16 h, at which time no further hydrogen gas evolves
(removed through a bubbler). The resulting product is distilled
through a 30-cm vacuum jacketed Vigreux column under
reduced pressure: 71.7 g (97% yield) of TIPS triflate;
bp 83–87°C/1.7 mmHg.
Check Digit Verification of cas no
The CAS Registry Mumber 80522-42-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,0,5,2 and 2 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 80522-42:
(7*8)+(6*0)+(5*5)+(4*2)+(3*2)+(2*4)+(1*2)=105
105 % 10 = 5
So 80522-42-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H21F3O3SSi/c1-7(2)18(8(3)4,9(5)6)16-17(14,15)10(11,12)13/h7-9H,1-6H3
80522-42-5Relevant articles and documents
A mild method for the replacement of a hydroxyl group by halogen: 2. unified procedure and stereochemical studies
Gati, Wafa,Munyemana, Fran?ois,Colens, Alain,Srour, Aladdin,Dufour, Mathilde,Vardhan Reddy, K. Harsha,Téchy, Brigitte,Rosse, Gérard,Schweiger, Ed,Qiao, Qi,Ghosez, Léon
, (2020/08/19)
N,N-Dimethyl- and N,N-diisopropyl-1-halo-2-methyl-l-propenylamines are readily available reagents for the mild deoxyhalogenation of alcohols and hydroxyacids. In this study we showed that the reactivity of the reagents can be tuned by varying the size of the alkyl groups on the reagents: the replacement of methyl by isopropyl groups led to a significant increase of reactivity. We then described a unified procedure for all deoxyhalogenations using the readily available α-chloroenamines as reagents with (bromination, iodination) or without (chlorination) an alkaline bromide or iodide. Finally, we showed that deoxyhalogenation reactions of secondary alcohols were highly stereospecific and generally occurred with inversion of configuration.
Controlling the Substitution Pattern of Hexasubstituted Naphthalenes by Aryne/Siloxyfuran Diels–Alder Additions: Regio- and Stereocontrolled Synthesis of Arizonin C1 Analogs
Neumeyer, Markus,Kopp, Julia,Brückner, Reinhard
, p. 2883 - 2915 (2017/06/06)
3,4-Dimethoxybenz-1-yne and 2-siloxylated furans without or with a bromine atom at C-3 undergo Diels–Alder reactions with orientational selectivity. Hydrolysis furnished a bromine-free or a bromine-containing naphthalene, respectively. Bromination of the former provided a regioisomer of the latter. Either of the two compounds was processed to give a variety of unnatural naphthoquinonopyrano-γ-lactones. This occurred by a succession of (1) Heck coupling, (2) asymmetric dihydroxylation, (3) oxa-Pictet–Spengler cyclization, and (4) oxidation. The fifteen monomeric naphthoquinonopyrano-γ-lactone structures that we prepared resemble the natural product (–)-arizonin C1 or its C-5 epimer. Accordingly, they represent hexasubstituted naphthalenes likewise. The sixteenth naphthoquinonopyrano-γ-lactone that we synthesized is a kind of dimer. Its moieties are bridged differently than those in naturally occurring naphthoquinonopyrano-γ-lactone dimers.
Process for producing novel naphthyridine derivatives
-
, (2008/06/13)
A novel naphthyridine derivative showing high activity as a tachykinin receptor antagonist can be produced at high efficiency by reacting an acylating agent such as a carboxylic acid derivative with a compound represented by the formula (1): wherein R1, R2 and R3 represent independently a hydrogen atom, a lower alkyl group, a lower alkoxyl group, an aryl group, a heteroaryl group, an amino group, etc., and X1 and X2 represent respectively a halogen atom.