252054-88-9

Basic information

• Product Name: 1-(TRIMETHYLSILYL)-2-NAPHTHYL TRIFLATE
• Synonyms: 1-(TRIMETHYLSILYL)-2-NAPHTHYL TRIFLATE;1-(TRIMETHYLSILYL)-2-NAPHTHYL TRIFLUOROMETHANESULFONATE,96.0+%(GC);1-(Trimethylsilyl)-2-naphthyl Trifluoromethanesulfonate;Trifluoromethanesulfonic Acid 1-(Trimethylsilyl)-2-naphthyl Ester;1-(Trimethylsilyl)-2-naphthyl Triflate Trifluoromethanesulfonic Acid 1-(Trimethylsilyl)-2-naphthyl Ester;Methanesulfonic acid, trifluoro-, 1-(triMethylsilyl)-2-naphthalenyl ester;1-(trimethylsilyl)-2-naphthyl trifluoromethansulfonate
• CAS NO: 252054-88-9
• 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: 252054-88-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 386.121°C at 760 mmHg
• Flash Point: 187.32°C
• Appearance: /
• Density: 1.28
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5250-1.5290
• Storage Temp.: 0-10°C
• CAS DataBase Reference: 1-(TRIMETHYLSILYL)-2-NAPHTHYL TRIFLATE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(TRIMETHYLSILYL)-2-NAPHTHYL TRIFLATE(252054-88-9)
• EPA Substance Registry System: 1-(TRIMETHYLSILYL)-2-NAPHTHYL TRIFLATE(252054-88-9)

Safety Data

• Statements: 34
• Safety Statements: 49-23-36-26-46
• RIDADR: 3265
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 252054-88-9(Hazardous Substances Data)

Usage

General Description

1-(Trimethylsilyl)-2-naphthyl triflate is a chemical compound with the formula C16H17F3O3Si. It is commonly used as a reagent in organic synthesis, particularly in the formation of carbon-carbon and carbon-heteroatom bonds. The triflate group in the compound is a good leaving group, making it useful for various reactions such as Suzuki-Miyaura coupling, Heck reaction, and Mitsunobu reaction. The trimethylsilyl group also provides stability and protection to the naphthyl group, allowing for selective transformations. Overall, 1-(Trimethylsilyl)-2-naphthyl triflate is a valuable reagent in organic chemistry for a wide range of synthetic applications.

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

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 53553-72-3 ((1-bromonaphthalen-2-yl)oxy)trimethylsilane 
• 573-97-7 1-bromo-2-naphthol 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 155351-49-8 (2-Bromo-naphthalen-1-yl)-trimethyl-silane 
• 771-15-3 2-bromo-1-naphthol 
• 18081-07-7 1-(trimethylsilyl)naphthalen-2-ol 
• 135-19-3 β-naphthol 

Downstream Products

• 1005386-15-1 C₄₃H₃₆BrNO₄S 
• 321-38-0 1-Fluoronaphthalene 
• 403646-52-6 1-(trifluoromethoxy)naphthalene 
• 403646-54-8 2-(trifluoromethoxy)naphthalene 
• 383909-27-1 C₆H₅CCC₁₀H₆Sn(C₄H₉)3 
• 383909-26-0 C₆H₅CCC₁₀H₆Sn(C₄H₉)3 
• 1096920-53-4 (4-bromophenyl)(naphthalen-1-yl)methanone 
• 760192-88-9 (4-bromophenyl) (naphthalen-2-yl)methanone 
• 1360569-91-0 4-methoxy-2-(naphthaken-2-yl)aniline 
• 1616349-17-7 C₂₆H₂₂Si 
• 27798-46-5 benzonaphtho<2,1-p>chrysene 

Relevant articles and documents

Small Gold(I) and Gold(I)–Silver(I) Clusters by C?Si Auration

Auration of o-trimethylsilyl arylphosphines leads to the formation of gold and gold–silver clusters with ortho-metalated phosphines displaying 3c–2e Au?C?M bonds (M=Au/Ag). Hexagold clusters [Au6L4](X)2 are obtained by reaction of (L?TMS)AuCl with AgX, whereas reaction with AgX and Ag2O leads to gold–silver clusters [Au4Ag2L4](X)2. Oxo-trigold(I) species [Au3O]+ were identified as the intermediates in the formation of the silver-doped clusters. Other [Au5], [Au4Ag], and [Au12Ag4] clusters were also obtained. Clusters containing PAu?Au?AuP structural motif display good catalytic activity in the activation of alkynes under homogeneous conditions.

Trifluoromethyl aryl sulfonates (TFMS): An applicable trifluoromethoxylation reagent

Fluorine is probably another favorite hetero-atom for incorporation into small molecules after nitrogen. Among many fluorine-containing groups, trifluoromethyl aryl ethers (ArOCF3) have unique properties in drug design and are difficult to be synthesized, and many different methods were developed to prepare them. A novel one-pot synthesis of o-iodine-aryl trifluoromethyl ethers (ArOCF3I) was described by the reaction of trifluoromethoxylation and iodination with trifluoromethyl aryl sulfonates (TFMS) in this manuscript. The reaction conditions were optimized by screening different solvents, crown ethers, substrates and the ratios and the yields of products were in moderate to high yields (up to 86%).

Continuous-flow synthesis of trimethylsilylphenyl perfluorosulfonate benzyne precursors

2-(Trimethylsilyl)phenyl perfluorosulfonated aryne precursors may now be accessed using flow chemistry, enabling the fast preparation of pure compounds with no requirement for low temperature lithiation or column chromatography. The process has been adapted to novel nonaflate precursors, utilizing the cheaper and more user-friendly nonaflyl fluoride reagent. The resultant nonaflates are shown to successfully participate in a range of aryne reaction classes.