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80522-42-5

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80522-42-5 Usage

Chemical Properties

clear light brown to orange-brown liquid

Physical properties

Colorless oil; bp 83–87 °C/1.7 mmHg; d 1.173 g cm?3.

Uses

Different sources of media describe the Uses of 80522-42-5 differently. You can refer to the following data:
1. Triisopropylsilyl Trifluoromethanesulfonate is a highly reactive silylating agent and Lewis acid capable of converting primary and secondary alcohols to the corresponding triisopropylsilyl ethers and converting ketones and lactones into their enol silyl ethers; protection of terminal alkynes; promoting conjugate addition of alkynylzinc compounds to α,β-enones; preparation of (triisopropylsilyl)diazomethane, participating in the following (but not limited to) reactions: Silylation of Alcohols, Formations of Enol Silyl Ethers, Alkynyltriisopropylsilanes, Conjugate Addition of Alkynylzinc Bromides, (Triisopropylsilyl)diazomethane, Triisopropylsiloxycarbonyl (Tsoc) and BIPSOP Protecting Groups for Amines, TIPS Protection for Oxazoles/Regioselective Trapping of C-2 Oxazole Anions, Benzannulation Using Triisopropylsilyl Vinyl Ketenes, Cyclization of 1-Silyloxy-1,5-diynes, Desymmetrization of Tartaric Acid Esters etc.
2. 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. As a protecting group in organic synthesis, it is utilized especially for the protection of primary amines. Furthermore, it plays an important role in Takahashi Taxol total synthesis or for chemical glycosylation reactions.

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

80522-42-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Price
  • Detail
  • TCI America

  • (T1588)  Triisopropylsilyl Trifluoromethanesulfonate  >98.0%(T)

  • 80522-42-5

  • 5g

  • 350.00CNY

  • Detail
  • TCI America

  • (T1588)  Triisopropylsilyl Trifluoromethanesulfonate  >98.0%(T)

  • 80522-42-5

  • 25g

  • 1,110.00CNY

  • Detail
  • Alfa Aesar

  • (B21127)  Triisopropylsilyl trifluoromethanesulfonate, 97%   

  • 80522-42-5

  • 5g

  • 348.0CNY

  • Detail
  • Alfa Aesar

  • (B21127)  Triisopropylsilyl trifluoromethanesulfonate, 97%   

  • 80522-42-5

  • 25g

  • 1148.0CNY

  • Detail
  • Alfa Aesar

  • (B21127)  Triisopropylsilyl trifluoromethanesulfonate, 97%   

  • 80522-42-5

  • 100g

  • 4247.0CNY

  • Detail
  • Aldrich

  • (248460)  Triisopropylsilyltrifluoromethanesulfonate  97%

  • 80522-42-5

  • 248460-10G

  • 739.44CNY

  • Detail
  • Aldrich

  • (248460)  Triisopropylsilyltrifluoromethanesulfonate  97%

  • 80522-42-5

  • 248460-50G

  • 2,808.00CNY

  • Detail

80522-42-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Triisopropylsilyl-trifluoromethanesulfonate

1.2 Other means of identification

Product number -
Other names tri(propan-2-yl)silyl trifluoromethanesulfonate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:80522-42-5 SDS

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.

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