Triisopropylsilyl Trifluoromethanesulfonate

Product Name: Triisopropylsilyl Trifluoromethanesulfonate
CAS No.: 80522-42-5
Chemical Name: Triisopropylsilyl Trifluoromethanesulfonate
Synonyms: TIPS-OTF;TRIISOPROPYLSILYL TRIFLATE;Triisopropylsilyl;(i-Pr)3SiOTf;TIPS TRIFLATE;Triisopropyl trifluoromethane sulfonate;TRIISOPROPYLSILYL TRIFLUOROMETHANESULPHONATE;DKFELEX0272;SILANE IP3-TRIFLATE;WACKER SILANE IP3-TRIFLATE
CBNumber: CB5189874
Molecular Formula: C10H21F3O3SSi
Formula Weight: 306.42
MOL File: 80522-42-5.mol

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Triisopropylsilyl Trifluoromethanesulfonate Property

Boiling point:: 45-46 °C/0.03 mmHg
Density: 1.14 g/mL at 25 °C (lit.)
refractive index: n20/D 1.415(lit.)
Flash point:: 213 °F
storage temp.: under inert gas (nitrogen or Argon) at 2-8°C
solubility: Miscible with chloroform and ethyl acetate.
form: Liquid
Specific Gravity: 1.14
color: Clear light brown to orange-brown
Sensitive: Moisture Sensitive
Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents
BRN: 3591541
InChI: InChI=1S/C10H21F3O3SSi/c1-7(2)18(8(3)4,9(5)6)16-17(14,15)10(11,12)13/h7-9H,1-6H3
InChIKey: LHJCZOXMCGQVDQ-UHFFFAOYSA-N
SMILES: C(F)(F)(F)S(O[Si](C(C)C)(C(C)C)C(C)C)(=O)=O
CAS DataBase Reference: 80522-42-5(CAS DataBase Reference)

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Safety

Hazard Codes: C
Risk Statements: 34
Safety Statements: 26-36/37/39-45-28A-27
RIDADR: UN 3265 8/PG 2
WGK Germany: 3
F: 3-10-21
TSCA: No
HazardClass: 8
PackingGroup: II
HS Code: 29319090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P363Wash contaminated clothing before reuse.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 248460
Product name: Triisopropylsilyl trifluoromethanesulfonate
Purity: 97%
Packaging: 10g
Price: $145
Updated: 2024/03/01

Sigma-Aldrich

Product number: 248460
Product name: Triisopropylsilyl trifluoromethanesulfonate
Purity: 97%
Packaging: 50g
Price: $237.6
Updated: 2024/03/01

TCI Chemical

Product number: T1588
Product name: Triisopropylsilyl Trifluoromethanesulfonate
Purity: >98.0%(T)
Packaging: 5g
Price: $28
Updated: 2024/03/01

TCI Chemical

Product number: T1588
Product name: Triisopropylsilyl Trifluoromethanesulfonate
Purity: >98.0%(T)
Packaging: 25g
Price: $102
Updated: 2024/03/01

Alfa Aesar

Product number: B21127
Product name: Triisopropylsilyl trifluoromethanesulfonate
Purity: 97%
Packaging: 5g
Price: $40.65
Updated: 2024/03/01

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Triisopropylsilyl Trifluoromethanesulfonate Chemical Properties,Usage,Production

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

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.

Uses

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.

Reactivity Profile

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).

References

[1] Rücker, C. “1,3‐Bis(triisopropylsilyl)propyne.” 2001. 0.
[2] Fumihiko Yoshimura. “Nucleophilic Addition of Alkanenitriles to Aldehydes via N-Silyl Ketene Imines Generated In Situ.” Synlett 29 1 (2017): 1816–1820.

Triisopropylsilyl Trifluoromethanesulfonate Preparation Products And Raw materials

Raw materials

Preparation Products

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Triisopropylsilyl Trifluoromethanesulfonate Suppliers

Belgium 3 China 236 France 2 Germany 5 India 9 Italy 1 Japan 3 Singapore 1 Switzerland 2 United Kingdom 9 United States 31 Global 302

Acros Organics (Part of Thermo Fisher Scientific )

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Alkemi BVBA

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Acros Organics

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View Lastest Price from Triisopropylsilyl Trifluoromethanesulfonate manufacturers

Hebei Weibang Biotechnology Co., Ltd

Product: TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE 80522-42-5
Price: US $10.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 100 mt
Release date: 2024-11-12

Hebei Mojin Biotechnology Co., Ltd

Product: TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE 80522-42-5
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 50000KG/month
Release date: 2023-08-30

LY Global chemicals co.,ltd .

Product: TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE 80522-42-5
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99.0%
Supply Ability: 1000KG
Release date: 2023-03-09

80522-42-5, Triisopropylsilyl TrifluoromethanesulfonateRelated Search:

Triethylsilane TRIETHYL 2-PHOSPHONOBUTYRATE Triethyloxonium tetrafluoroborate FLUOROTRIETHYLSILANE TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE Chlorotriethylsilane Sodium triacetoxyborohydride acetic acid, triethoxy-, ethyl ester triisopropylsilyl Methacrylate Triethylamine trihydrofluoride Triisopropylsilyl chloride Trimethoxysilane TRIFLUOROMETHANESULFONIC ACID DIETHYLISOPROPYLSILYL ESTER TrimethylSilyl Trifluoromethanesulfonate TRIETHYLSILANOL TRIMETHYLSILYL METHANESULFONATE Triisopropylsilane Triethylsilyl trifluoromethanesulfonate

Triisopropyl(trifluoromethylsulfonyloxy)silane

Triisopropylsilyl-trifluoromethanesulfonate,97%

Triisopropylsilyl

Triisopropylsilyl Triflate Trifluoromethanesulfonic Acid Triisopropylsilyl Ester

Triisopropyl trifluoromethane sulfonate

Triisopropylsilyl trifluoromethanesulfonate ,98%

(i-Pr)3SiOTf

Triisopropylsilyl-trifluoroMethanesulfonate, 97% 10GR

RIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE

1,1,1-TrifluoroMethanesulfonic Acid Tris(1-Methylethyl)silyl Ester

TRIISOPROPYLSILYL TRIFLUOROMETHANESULFOTE

TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE, 97%TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE, 97%TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE, 97%

TRI ISOPROPYLSILYL TRIFLUOROMETHANESULPHONATE 98%

SILANE IP3-TRIFLATE

TIPS-OTF

TIPS TRIFLATE

TRIFLUOROMETHANESULFONIC ACID TRIISOPROPYLSILYL ESTER

TRIISOPROPYLSILYL TRIFLATE

TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE

TRIISOPROPYLSILYL TRIFLUOROMETHANESULPHONATE

WACKER SILANE IP3-TRIFLATE

TIPS triflate, Trifluoromethanesulfonic acid triisopropylsilyl ester, Triisopropylsilyl triflate

TIPS triflate, Trifluoromethanesulfonic acid triisopropylsilyl ester, Triisopropylsilyl triflate, Wacker Silane IP3-triflate

TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE 97%

Trifluormethansulfons?ure-tris(1-methylethyl)-silylester

Methanesulfonic acid, 1,1,1-trifluoro-, tris(1-methylethyl)silyl ester

TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE ISO 9001：2015 REACH

80522-42-5 TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE

tri(propan-2-yl)silyl trifluoromethanesulfonate

TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE TIPS triflate, Triisopropylsilyl triflate

DKFELEX0272

80522-42-5

C10H21F3O3SSi

CF3SO3SiCHCH323

Synthetic Reagents

Silicon-Based

Protecting and Derivatizing Reagents

Protection and Derivatization

Silyl Esters

Protection & Derivatization Reagents (for Synthesis)

Silicon Compounds (for Synthesis)

Si (Classes of Silicon Compounds)

Si-O Compounds

Protection & Derivatization Reagents (for Synthesis)

Si (Classes of Silicon Compounds)

Silicon Compounds (for Synthesis)

Silyl Esters

Si-O Compounds

Synthetic Organic Chemistry