Triisopropylsilyl trifluoromethanesulfonate

Name: Triisopropylsilyl trifluoromethanesulfonate
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CAS No. 80522-42-5
Cat. No. CS-B0888
Purity≥95%
MDL No.MFCD00009913

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Triisopropylsilyl trifluoromethanesulfonate|CS-B0888

Structure of 80522-42-5

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General Information

CAS No. 80522-42-5
Cat. No. CS-B0888
Purity ≥95%
MDL No. MFCD00009913
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₂₁F₃O₃SSi
Molecular Weight 306.42
Synonym(s) tris(1-methylethyl)silyl trifluoromethanesulfonate
SMILES O=S(C(F)(F)F)(O[Si](C(C)C)(C(C)C)C(C)C)=O

Description

Used to prepare silyloxy acetylenes from lithium acetylides; the silyloxy acetylenes were then employed in protic acid-promoted cyclizations of arenes, alkynes and olefins.

Application

Triisopropylsilyl trifluoromethanesulfonate serves as a highly effective silylating agent for the protection of alcohols and carboxylic acids, enabling rapid formation of stable silyl ethers under mild conditions. Its bulky triisopropylsilyl group provides excellent steric shielding, enhancing functional group stability during subsequent transformations. The triflate leaving group ensures high reactivity in nucleophilic substitution reactions, facilitating efficient deprotection with fluoride sources. This reagent exhibits excellent bench stability, ease of handling, and compatibility with complex molecular architectures, making it a reliable choice for synthetic workflows requiring orthogonal protection strategies.

Synthesis

Route1
- In-stock
  
  6485-79-6
- 1493-13-6
- ~98%
- In-stock
  
  80522-42-5
References
- Tetrahedron Letters, , vol. 22, # 36 p. 3455 - 3458
Route2
- 1493-13-6
- In-stock
  
  24400-84-8
- ~%
- In-stock
  
  80522-42-5
References
- Synthesis, , # 7 p. 744 - 746
Route3
- 13154-24-0
- 1493-13-6
- ~%
- In-stock
  
  80522-42-5
References
- Bulletin of the Chemical Society of Japan, , vol. 63, # 4 p. 1039 - 1048 Tetrahedron Letters, , vol. 28, # 49 p. 6191 - 6194

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS05
Signal Word : Danger	UN#: 3265
Class : 8	Packing Group : Ⅱ
Hazard Statements : H314
Precautionary Statements : P260-P264-P280-P301+P330+P331-P304+P340-P363-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 43.37
LogP 4.0281
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 5

Other Classifications

Building Blocks Skeleton Fatty chain compounds

Material Science Organic-Inorganic Hybrid Materials A silane coupling agent

Chemical Synthesis Organometallic Reagents Organosilicon Carboxylic Acid Silyl Esters, Sulfonic Acid Silyl Esters

Chemical Synthesis Synthetic Reagents Protection, Deprotection, Derivatization Protecting and Derivatizing Reagents

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Triisopropylsilyl trifluoromethanesulfonate

CAS No. 80522-42-5

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