| Identification | More | [Name]
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE | [CAS]
80522-42-5 | [Synonyms]
SILANE IP3-TRIFLATE
TIPS-OTF
TIPS TRIFLATE
TRIFLUOROMETHANESULFONIC ACID TRIISOPROPYLSILYL ESTER
TRIISOPROPYLSILYL TRIFLATE
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE
TRIISOPROPYLSILYL TRIFLUOROMETHANESULPHONATE
WACKER SILANE IP3-TRIFLATE
TRI ISOPROPYLSILYL TRIFLUOROMETHANESULPHONATE 98%
TRIISOPROPYLSILYL TRIFLUOROMETHANESULFONATE 97%
TIPS triflate, Trifluoromethanesulfonic acid triisopropylsilyl ester, Triisopropylsilyl triflate, Wacker Silane IP3-triflate
TIPS triflate, Trifluoromethanesulfonic acid triisopropylsilyl ester, Triisopropylsilyl triflate
Triisopropyl(trifluoromethylsulfonyloxy)silane | [EINECS(EC#)]
638-988-6 | [Molecular Formula]
C10H21F3O3SSi | [MDL Number]
MFCD00009913 | [Molecular Weight]
306.42 | [MOL File]
80522-42-5.mol |
| Chemical Properties | Back Directory | [Appearance]
clear light brown to orange-brown liquid | [Boiling point ]
45-46 °C/0.03 mmHg | [density ]
1.14 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.415(lit.)
| [Fp ]
213 °F
| [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Miscible with chloroform and ethyl acetate. | [form ]
Liquid | [color ]
Clear light brown to orange-brown | [Specific Gravity]
1.14 | [Hydrolytic Sensitivity]
8: reacts rapidly with moisture, water, protic solvents | [Sensitive ]
Moisture Sensitive | [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 Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S27:Take off immediately all contaminated clothing . | [RIDADR ]
UN 3265 8/PG 2
| [WGK Germany ]
3
| [F ]
3-10-21 | [TSCA ]
No | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [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. | [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.
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