780820-43-1

Basic information

• Product Name: 3-(TRIMETHYLSILYL)-2-NAPHTHYL TRIFLUOROMETHANESULFONATE
• Synonyms: 3-(TRIMETHYLSILYL)-2-NAPHTHYL TRIFLUOROMETHANESULFONATE;3-(TRIMETHYLSILYL)-2-NAPHTHYL TRIFLUOROMETHANESULFONATE,95.0+%(GC);3-(Trimethylsilyl)-2-naphthyl Triflate;Trifluoromethanesulfonic Acid 3-(Trimethylsilyl)-2-naphthyl Ester;3-(Trimethylsilyl)-2-naphthyl Triflate Trifluoromethanesulfonic Acid 3-(Trimethylsilyl)-2-naphthyl Ester;Methanesulfonic acid, trifluoro-, 3-(triMethylsilyl)-2-naphthalenyl ester
• CAS NO: 780820-43-1
• Molecular Formula: C14H15F3O3SSi
• Molecular Weight: 348.41
• Product Categories: Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry
• Mol File: 780820-43-1.mol

Chemical Properties

• Boiling Point: 386.121°C at 760 mmHg
• Flash Point: 187.32°C
• Appearance: /
• Density: 1.26
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5180 to 1.5210
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 3-(TRIMETHYLSILYL)-2-NAPHTHYL TRIFLUOROMETHANESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(TRIMETHYLSILYL)-2-NAPHTHYL TRIFLUOROMETHANESULFONATE(780820-43-1)
• EPA Substance Registry System: 3-(TRIMETHYLSILYL)-2-NAPHTHYL TRIFLUOROMETHANESULFONATE(780820-43-1)

Safety Data

• Statements: 34
• Safety Statements: 49-36-62-26
• RIDADR: 3265
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 780820-43-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-(TRIMETHYLSILYL)-2-NAPHTHYL TRIFLUOROMETHANESULFONATE is used as a reagent for the introduction of the 2-naphthyl group in organic synthesis. Its application is crucial for the creation of complex organic molecules and the development of new pharmaceuticals and materials.
Used in the Diels-Alder Reaction:
In the field of organic chemistry, 3-(TRIMETHYLSILYL)-2-NAPHTHYL TRIFLUOROMETHANESULFONATE is used as a catalyst in the Diels-Alder reaction, a fundamental [4+2] cycloaddition process. It enhances the reaction's efficiency and selectivity, leading to the formation of valuable six-membered ring compounds.
Used in the Suzuki-Miyaura Coupling:
3-(TRIMETHYLSILYL)-2-NAPHTHYL TRIFLUOROMETHANESULFONATE also serves as a catalyst in the Suzuki-Miyaura coupling, a cross-coupling reaction between an organoboron compound and an organic halide. This reaction is essential for the formation of carbon-carbon bonds, which are prevalent in the synthesis of biologically active molecules and advanced materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-(TRIMETHYLSILYL)-2-NAPHTHYL TRIFLUOROMETHANESULFONATE is used as a key intermediate in the synthesis of various drugs. Its ability to form carbon-carbon and carbon-heteroatom bonds is crucial for the development of new medicinal compounds with improved therapeutic properties.
Used in Material Science:
3-(TRIMETHYLSILYL)-2-NAPHTHYL TRIFLUOROMETHANESULFONATE is utilized in material science for the synthesis of advanced materials with unique properties. Its application in the formation of carbon-carbon bonds contributes to the development of new polymers, composites, and other materials with potential applications in various industries.

InChI:InChI=1/C14H15F3O3SSi/c1-22(2,3)13-9-11-7-5-4-6-10(11)8-12(13)20-21(18,19)14(15,16)17/h4-9H,1-3H3

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 30478-88-7 3-bromo-2-naphthol 
• 68251-77-4 2‐bromo‐3‐methoxynaphthalene 
• 93-04-9 2-Methoxynaphthalene 

Downstream Products

• 82158-50-7 naphtho[2,3-b]furan-2-yl(phenyl)methanone 
• 196-62-3 trinaphthylene 
• 32338-05-9 2-(phenylsulfonyl)naphthalene 
• 1411714-70-9 1,1-dimethyl-2,3-diphenyl-1H-naphtho[2,3-b]silole 
• 1607828-70-5 C₃₁H₂₃N 

Relevant articles and documents

Transition-Metal-Free Benzannulation of Tricarbonyl Derivatives with Arynes: Access to 1,3-Dinaphthol Precursors for the Synthesis of Rhodamine Dye Analogues

Herein, we report a transition-metal-free annulation reaction of benzynes and 1,3-oxopentanedioate for the synthesis of highly functionalized naphthalene derivatives for the first time. Additionally, the representative naphthalene derivatives have been successfully transformed into the new series of rhodamine dye analogues.

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.

2-(Trimethylsilyl)phenyl Trimethylsilyl Ethers as Stable and Readily Accessible Benzyne Precursors

Stable 2-(trimethylsilyl)phenyl trimethylsilyl ethers, readily obtained from the corresponding halogenated phenols in two steps, were identified as novel benzyne precursors. These species were converted to benzynes by a domino reaction of O-desilylation,

Access to Air-Stable 1,3-Diphosphacyclobutane-2,4-diyls by an Arylation Reaction with Arynes

Tuning of the physicochemical properties of the 1,3-diphosphacyclobutane-2,4-diyl unit is attractive in view of materials applications. The use of arynes is shown to be effective for installing relatively electron rich aryl substituents into the open-shell singlet P-heterocyclic system. Treatment of the sterically encumbered 1,3-diphosphacyclobuten-4-yl anion with ortho-silylated aryl triflates in the presence of fluoride under appropriate conditions afforded the corresponding 1-aryl 1,3-diphosphacyclobutane-2,4-diyls. The air-stable open-shell singlet P-heterocycles exhibit considerable electron-donating character, and the aromatic substituent influences the open-shell character, which is thought to be related to the property of p-type semiconductivity. The P-arylated 1,3-diphosphacyclobutane-2,4-diyl systems can be further utilized as detectors of hydrogen fluoride (HF), which causes a remarkable change in their photoabsorption properties.