Production Method 1

13154-24-0

1493-13-6

80522-42-5

Reaction Conditions

Reference

Invesitigations into a Stereoselective Total Synthesis of Polyoxygenated Cembranoids

Hoelsken, Soeren, 2004, , ,

Production Method 2

1493-13-6

6485-79-6

80522-42-5

Reaction Conditions

Reference

Studies with trialkylsilyltrifluoromethylsulfonates: new syntheses and applications

Corey, E. J.; et al, Tetrahedron Letters, 1981, 22(36), 3455-8

Production Method 3

1493-13-6

6485-79-6

80522-42-5

Reaction Conditions

1.1 0 °C; 1 h, 0 °C; 0 °C → rt; 17 h, rt

Reference

Controlling the Substitution Pattern of Hexasubstituted Naphthalenes by Aryne/Siloxyfuran Diels-Alder Additions: Regio- and Stereocontrolled Synthesis of Arizonin C1 Analogs

Neumeyer, Markus; et al, European Journal of Organic Chemistry, 2017, 2017(20), 2883-2915

Triisopropylsilyl trifluoromethanesulfonate Raw materials

• chlorotris(propan-2-yl)silane
• Trifluoromethanesulfonic acid
• Triisopropylsilane

Triisopropylsilyl trifluoromethanesulfonate Preparation Products

• Triisopropylsilyl trifluoromethanesulfonate (80522-42-5)

• 1. Dissolution of cork biopolymers in biocompatible ionic liquids
  Helga Garcia,Rui Ferreira,Marija Petkovic,Jamie L. Ferguson,Maria C. Leit?o,H. Q. Nimal Gunaratne,Luís Paulo N. Rebelo Green Chem., 2010,12, 367-369
• 2. Dissociation of large gaseous serine clusters produces abundant protonated serine octamer
  Jacob S. Jordan,Evan R. Williams Analyst, 2021,146, 2617-2625
• 3. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
  Analyst, 1996,121, 785-788
• 4. Evidence of pre-micellar aggregates in aqueous solution of amphiphilic PDMS–PEO block copolymer?
  Domenico Lombardo,Gianmarco Munaò,Pietro Calandra,Luigi Pasqua,Maria Teresa Caccamo Phys. Chem. Chem. Phys., 2019,21, 11983-11991
• 5. Evidence of rutile-to-anatase photo-induced electron transfer in mixed-phase TiO2 by solid-state NMR spectroscopy?
  Weili Dai,Guangjun Wu,Michael Hunger Chem. Commun., 2015,51, 13779-13782

• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Organic sulfonic acids and derivatives Organosulfonic acids and derivatives Alkanesulfonic acids and derivatives
• Solvents and Organic Chemicals Organic Compounds

Introduction to Triisopropylsilyl trifluoromethanesulfonate (CAS No. 80522-42-5)

Triisopropylsilyl trifluoromethanesulfonate, with the chemical formula (C?H??FO?S), is a highly specialized organosilicon compound widely utilized in the field of organic synthesis and pharmaceutical development. Its CAS number, 80522-42-5, uniquely identifies it in scientific and industrial databases, underscoring its significance in modern chemical applications. This compound serves as a crucial reagent in the protection and deprotection of functional groups, particularly in the synthesis of complex molecules such as pharmaceuticals and fine chemicals.

The primary utility of Triisopropylsilyl trifluoromethanesulfonate lies in its role as a silylating agent. Silylation reactions are fundamental in organic chemistry, enabling the introduction of silicon-based protecting groups that enhance the stability of sensitive functional groups during synthetic pathways. The trifluoromethanesulfonate (triflates) moiety in this compound contributes to its high reactivity and efficiency in facilitating these transformations. Specifically, it is employed to protect alcohols and thiols, allowing for selective modifications elsewhere in the molecule without interference from these reactive sites.

In recent years, advancements in synthetic methodologies have highlighted the importance of efficient protecting group strategies. Triisopropylsilyl trifluoromethanesulfonate has emerged as a preferred choice due to its ability to form stable derivatives that are easily removable under mild conditions. This characteristic is particularly valuable in multi-step syntheses where harsh conditions could degrade sensitive intermediates. The compound’s compatibility with a wide range of solvents and reaction conditions further enhances its appeal in industrial applications.

One of the most compelling aspects of Triisopropylsilyl trifluoromethanesulfonate is its application in pharmaceutical research. The demand for innovative drug candidates has driven the need for sophisticated synthetic tools, and silylating agents like this one play a pivotal role. For instance, recent studies have demonstrated its effectiveness in the synthesis of bioactive molecules targeting neurological disorders. The ability to selectively protect and deprotect functional groups allows chemists to construct complex drug scaffolds with high precision, ultimately leading to more effective therapeutic agents.

The compound’s stability under various reaction conditions also makes it suitable for large-scale production processes. In industrial settings, consistency and reproducibility are paramount, and Triisopropylsilyl trifluoromethanesulfonate meets these criteria by maintaining its integrity throughout multiple synthetic cycles. This reliability has made it a staple in pharmaceutical manufacturing, where even minor deviations can impact yield and purity.

Furthermore, environmental considerations have influenced the development of greener chemical alternatives. While Triisopropylsilyl trifluoromethanesulfonate is not inherently environmentally friendly, its efficiency in synthetic processes reduces the need for excess reagents or harsh conditions, thereby minimizing waste generation. Future research may focus on developing analogous compounds that offer similar functionality but with reduced environmental impact.

Recent breakthroughs in computational chemistry have also enhanced our understanding of how Triisopropylsilyl trifluoromethanesulfonate interacts with other molecular entities. By leveraging computational models, researchers can predict reaction outcomes with greater accuracy, optimizing synthetic routes before experimental trials. This approach not only saves time but also resources, making drug discovery more cost-effective.

The versatility of Triisopropylsilyl trifluoromethanesulfonate extends beyond pharmaceutical applications. It is also widely used in materials science, where it contributes to the development of advanced polymers and coatings. The ability to modify polymer backbones through silylation reactions opens up new possibilities for creating materials with tailored properties such as enhanced durability or biodegradability.

In conclusion, Triisopropylsilyl trifluoromethanesulfonate (CAS No. 80522-42-5) represents a cornerstone in modern organic synthesis. Its role as a versatile silylating agent has been instrumental in advancing both academic research and industrial applications. As scientific understanding continues to evolve, this compound will undoubtedly remain a critical tool for chemists seeking innovative solutions to complex synthetic challenges.

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