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;DKSI152;DKFELEX0272;SILANE IP3-TRIFLATE
- CBNumber
- CB5189874
- Molecular Formula
- C10H21F3O3SSi
- Formula Weight
- 306.42
- MOL File
- 80522-42-5.mol
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)
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
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.
N-Bromosuccinimide Price
- Product number
- 248460
- Product name
- Triisopropylsilyl trifluoromethanesulfonate
- Purity
- 97%
- Packaging
- 10g
- Price
- $145
- Updated
- 2024/03/01
- Product number
- 248460
- Product name
- Triisopropylsilyl trifluoromethanesulfonate
- Purity
- 97%
- Packaging
- 50g
- Price
- $237.6
- Updated
- 2024/03/01
- Product number
- T1588
- Product name
- Triisopropylsilyl Trifluoromethanesulfonate
- Purity
- >98.0%(T)
- Packaging
- 5g
- Price
- $28
- Updated
- 2024/03/01
- Product number
- T1588
- Product name
- Triisopropylsilyl Trifluoromethanesulfonate
- Purity
- >98.0%(T)
- Packaging
- 25g
- Price
- $102
- Updated
- 2024/03/01
- Product number
- B21127
- Product name
- Triisopropylsilyl trifluoromethanesulfonate
- Purity
- 97%
- Packaging
- 5g
- Price
- $40.65
- Updated
- 2024/03/01
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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View Lastest Price from Triisopropylsilyl Trifluoromethanesulfonate manufacturers
- 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
- 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
- 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