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;DKSI152;DKFELEX0272;SILANE IP3-TRIFLATE
- CBNumber:
- CB5189874
- Molecular Formula:
- C10H21F3O3SSi
- Molecular Weight:
- 306.42
- MDL Number:
- MFCD00009913
- MOL File:
- 80522-42-5.mol
| Boiling point | 45-46 °C/0.03 mmHg |
|---|---|
| Density | 1.14 g/mL at 25 °C (lit.) |
| refractive index |
n |
| 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) |
| UNSPSC Code | 12352001 |
| NACRES | NA.22 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS05 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H314 | |||||||||
| Precautionary statements | P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363-P405 | |||||||||
| 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 | |||||||||
| NFPA 704 |
|
Triisopropylsilyl Trifluoromethanesulfonate price More Price(27)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 248460 | Triisopropylsilyl trifluoromethanesulfonate 97% | 80522-42-5 | 10g | $145 | 2024-03-01 | Buy |
| Sigma-Aldrich | 248460 | Triisopropylsilyl trifluoromethanesulfonate 97% | 80522-42-5 | 50g | $237.6 | 2024-03-01 | Buy |
| TCI Chemical | T1588 | Triisopropylsilyl Trifluoromethanesulfonate >98.0%(T) | 80522-42-5 | 5g | $28 | 2024-03-01 | Buy |
| TCI Chemical | T1588 | Triisopropylsilyl Trifluoromethanesulfonate >98.0%(T) | 80522-42-5 | 25g | $102 | 2024-03-01 | Buy |
| Alfa Aesar | B21127 | Triisopropylsilyl trifluoromethanesulfonate 97% | 80522-42-5 | 5g | $40.65 | 2024-03-01 | Buy |
Triisopropylsilyl Trifluoromethanesulfonate Chemical Properties,Uses,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 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.
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.
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
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Aceschem Inc. | +1-817863-6948 +1-（817）863-6948 | sales@aceschem.com | United States | 19632 | 58 |
| Jiangsu Vcan Advanced Material Co., Ltd. | +86-17306299870 +86-18652789875 | vcanam@vcanam.com | China | 38 | 58 |
| Hebei Weibang Biotechnology Co., Ltd | +8615531157085 | abby@weibangbio.com | China | 8804 | 58 |
| Hebei Mujin Biotechnology Co.,Ltd | +86 13288715578 +8613288715578 | sales@hbmojin.com | China | 12829 | 58 |
| Shanghai Daken Advanced Materials Co.,Ltd | +86-371-66670886 | info@dakenam.com | China | 19918 | 58 |
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | info@tianfuchem.com | China | 21632 | 55 |
| Hangzhou FandaChem Co.,Ltd. | 008657128800458; +8615858145714 | FandaChem@Gmail.com | China | 8252 | 55 |
| Fluoropharm Co., Ltd. | +86-0571-85586753; +8613336034509 | sales@fluoropharm.com | China | 1376 | 60 |
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | ivan@atkchemical.com | China | 32965 | 60 |
| Zjartschem | +86-571 87238903 | jocelynpan@zjarts.com | CHINA | 988 | 58 |
View Lastest Price from Triisopropylsilyl Trifluoromethanesulfonate manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2025-02-14 | TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE
80522-42-5
|
US $0.00 / KG | 1KG | 99% | 50000KG/month | Hebei Mujin Biotechnology Co.,Ltd | |
 |
2024-11-12 | TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE
80522-42-5
|
US $10.00 / kg | 1kg | 99% | 100 mt | Hebei Weibang Biotechnology Co., Ltd | |
 |
2023-03-10 | TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE
80522-42-5
|
US $0.00 / KG | 1KG | 99.0% | 1000KG | LY Global chemicals co.,ltd . |
-
- TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE
80522-42-5
- US $0.00 / KG
- 99%
- Hebei Mujin Biotechnology Co.,Ltd
-
- TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE
80522-42-5
- US $10.00 / kg
- 99%
- Hebei Weibang Biotechnology Co., Ltd
-
- TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE
80522-42-5
- US $0.00 / KG
- 99.0%
- LY Global chemicals co.,ltd .
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