88284-48-4

Basic information

• Product Name: 2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE
• Synonyms: 2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE;2-(trimethylsilyl)phenyl trifluoromethane-sulfona;2-(Trimethylsilyl)phenyl Triflate;Trifluoromethanesulfonic Acid 2-(Trimethylsilyl)phenyl Ester;2-(Trimethylsilyl)phenyl Triflate Trifluoromethanesulfonic Acid 2-(Trimethylsilyl)phenyl Ester;(TriMethylsilyl)phenyl Triflate;TriMethylsilyl)phenyl trifluoroMethanesulfona;2-(TriMethylsilyl)phenyl trifluoroMethanesulfonate 97%
• CAS NO: 88284-48-4
• Molecular Formula: C₁₀H₁₃F₃O₃SSi
• Molecular Weight: 298.35
• Product Categories: Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry;Organic Triflates;Organic Building Blocks;Sulfur Compounds
• Mol File: 88284-48-4.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 70 °C2 mm Hg(lit.)
• Flash Point: 205 °F
• Appearance: /
• Density: 1.229 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.456(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE(88284-48-4)
• EPA Substance Registry System: 2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE(88284-48-4)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: Ⅱ
• Hazardous Substances Data: 88284-48-4(Hazardous Substances Data)

Usage

Description

2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE, also known as 2-(Trimethylsilyl)phenyl Triflate, is a chemical reagent with a trimethylsilyl group attached to a phenyl ring and a trifluoromethanesulfonate group. It is known for its reactivity and ability to generate benzyne under mild conditions.

Uses

Used in Organic Synthesis:
2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE is used as a reagent for various organic synthesis applications, including reactions of polycyclic arenes, heteroatom arylation, heterocycles, and benzannulated heterocycles. Its reactivity allows for the formation of carbon-carbon and carbon-heteroatom bonds, making it a versatile tool in organic chemistry.
Used in Benzyne Generation:
2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE is used as a reagent for generating benzyne under mild conditions of simple fluoride treatment at room temperature. Benzyne is an important intermediate in organic synthesis, and its generation using this reagent allows for the formation of various functionalized aromatic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE is used as a reagent for the synthesis of various drug molecules. Its ability to form carbon-carbon and carbon-heteroatom bonds makes it useful in the development of novel pharmaceutical compounds with potential therapeutic applications.
Used in Material Science:
In material science, 2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE is used as a reagent for the synthesis of functionalized polymers and materials. Its reactivity allows for the formation of various polymer structures with potential applications in areas such as electronics, sensors, and coatings.

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 15288-53-6 o-(trimethylsilyl)phenol 
• 72525-60-1 hexamethyldisilazan 
• 95-56-7 2-hydroxybromobenzene 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 17878-37-4 1-bromo-2-(trimethylsilyl)benzene 
• 95-57-8 2-monochlorophenol 
• 17881-65-1 (2-chlorophenoxy)trimethylsilane 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 36601-47-5 2-bromophenyl trimethylsilyl ether 
• 18036-83-4 o-(trimethylsilyl)phenol trimethylsilyl ether 

Downstream Products

• 217-59-4 triphenylene 
• 232611-22-2 9-ethyl 10-methylphenanthrene-9-carboxylate 
• 68684-64-0 9-ethyl-10-phenylphenanthrene 
• 119-61-9 benzophenone 
• 79249-48-2 6-phenyl-6H-dibenzo[b,d]thiopyran 
• 87544-20-5 o-bis(allyl)benzene 
• 883-20-5 9-methylphenanthrene 
• 90-96-0 bis(p-methoxyphenyl)methanone 
• 611-97-2 bis(p-methylphenyl)-methanone 
• 186192-49-4 3-Methyl-10-p-tolyl-4aH-9-thia-phenanthrene 
• 91620-99-4 benzene-1,2,3,4,5,6-hexacarboxylic acid hexaethyl ester 

Relevant articles and documents

Benzyne-Mediated Esterification Reaction

A benzyne-mediated esterification of carboxylic acids and alcohols under mild conditions has been realized, which is made possible via a selective nucleophilic addition of carboxylic acid to benzyne in the presence of alcohol. After a subsequent transesterification with alcohol, the corresponding esters can be produced efficiently. This benzyne-mediated protocol can be used on the modification of Ibuprofen, cholesterol, estradiol, and synthesis of nandrolone phenylpropionate. In addition, benzyne can also be used to promote lactonization and amidation reaction.

Benzyne 1,2,4-Trisubstitution and Dearomative 1,2,4-Trifunctionalization

Both 1,2,4-trisubstitution and dearomative 1,2,4-trifunctionalization of benzyne have been accomplished from sulfoxides bearing a penta-2,4-dien-1-yl moiety. These cascade transformations proceed through a benzyne insertion into the S═O bond and an uncommon regiospecific anionic [4,5]-sigmatropic rearrangement, furnishing a C-O, C-S, and C-C bond on the C1-, C2-, and C4-position of a benzene ring, respectively. This study showcases new cascade benzyne reaction modes involving both distal C-H bond functionalization and dearomatization.

Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization

A highly efficient transition-metal-free general method for the synthesis of polycyclic aromatic hydrocarbons like phenanthrenes and chrysenes (and tetraphene) from β-bromovinylarenes and arynes has been developed. The reactions proceed via an aryne Diels-Alder (ADA) reaction, followed by a facile aromatization. This is the first report on direct construction of chrysenes (and tetraphene) using the ADA approach. Unlike the literature method which is limited to only 9/10-substituted derivatives, this method gives access to a wide variety of functionalized phenanthrenes.