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

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

Uses

Used in Organic Synthesis:
1-(Trimethylsilyl)-2-naphthyl triflate is used as a reagent for the formation of carbon-carbon and carbon-heteroatom bonds in organic synthesis. Its triflate group facilitates various reactions, such as Suzuki-Miyaura coupling, Heck reaction, and Mitsunobu reaction, making it a valuable tool for chemists in constructing complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-(Trimethylsilyl)-2-naphthyl triflate is used as a key intermediate in the synthesis of various drug molecules. Its ability to form stable intermediates and participate in selective transformations allows for the development of novel therapeutic agents with improved pharmacological properties.
Used in Material Science:
1-(Trimethylsilyl)-2-naphthyl triflate is also utilized in material science for the synthesis of advanced materials with specific properties. Its involvement in the formation of carbon-heteroatom bonds can lead to the development of new polymers, coatings, and other materials with unique characteristics for various 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 
• 155351-49-8 (2-Bromo-naphthalen-1-yl)-trimethyl-silane 
• 135-19-3 β-naphthol 
• 573-97-7 1-bromo-2-naphthol 
• 18081-07-7 1-(trimethylsilyl)naphthalen-2-ol 
• 771-15-3 2-bromo-1-naphthol 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 53553-72-3 ((1-bromonaphthalen-2-yl)oxy)trimethylsilane 

Downstream Products

• 1096920-53-4 (4-bromophenyl)(naphthalen-1-yl)methanone 
• 760192-88-9 (4-bromophenyl) (naphthalen-2-yl)methanone 
• 574-96-9 1-hydroxy-2-naphthaldehyde 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 
• 1338362-92-7 2-phenyl-2H-benzo[e]indazole 
• 57615-66-4 ethyl 3-phenyl-1H-benzo[g]indole-2-carboxylate 
• 1201835-73-5 phenyl-(2-phenylaminonaphthalen-1-yl)methanone 
• 1198298-08-6 10-(2-bromophenyl)-8,9-dihydro-10H-6b,9a-diazapentaleno[2,1-a]naphthalen-7-one 
• 1198298-09-7 7-(2-bromophenyl)-8,9-dihydro-7H-7a,10a-diazapentaleno[1,2-a]naphthalen-10-one 
• 1078120-48-5 1-benzyl-1H-naphtho[1,2-d][1,2,3]triazole 
• 1270170-25-6 1-benzyl-1H-naphtho[2,3-d][1,2,3]triazole 
• 383909-27-1 C₆H₅CCC₁₀H₆Sn(C₄H₉)3 
• 383909-26-0 C₆H₅CCC₁₀H₆Sn(C₄H₉)3 
• 321-38-0 1-Fluoronaphthalene 

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.

A Three-Phase Four-Component Coupling Reaction: Selective Synthesis of o-Chloro Benzoates by KCl, Arynes, CO2, and Chloroalkanes

A transition-metal-free three-phase four-component coupling reaction (3P-4CR) involving KCl, arynes, chloroalkanes and CO2 has been reported for the first time, enabling the incorporation of both chloro and CO2 into an aryne simultaneously. The reactions for the synthesis of different types of o-chloro benzoates can be selectively modulated by the chloroalkane utilized. The corresponding products can be alternatively transformed for postsynthetic functionalizations conveniently.

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%).

Selective: S -arylation of 2-oxazolidinethiones and selective N -arylation of 2-benzoxazolinones/2-benzimidazolinones

There exist three possible patterns for the reaction of cyclic 2-oxazolidinethione and 2-benzoxazolidinethione with arynes, namely (a) S-arylation, (b) N-arylation, and (c) aryne insertion into the thiocarbonyl group (CS). Our studies demonstrate that S-arylation wins out affording S-aryl dihydrooxazoles. In contrast, for related reactions of cyclic 2-benzoxazolinone and 2-benzimidazolinone with arynes, it is found that N-arylation outcompetes O-arylation and aryne insertion into the CO group to give N-aryl 2-benzoxazolinones and N-aryl 2-benzimidazolinones.

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.

Insertion of arynes into arylphosphoryl amide bonds: One-step simultaneous construction of C-N and C-P bonds

The insertion of arynes into arylphosphoryl amide bonds to synchronously construct C-P and C-N bonds is described. Arynes generated in situ from o-triflate arylsilanes under fluoride-promoted conditions insert into relatively inert P-N bonds, producing o-

Synthesis of aryl stannanes from silyl triflates via aryne intermediates

Aryl stannanes are easily accessible from o-silylated aryl triflates in the presence of KF and Bu3SnH. The corresponding arynes are formed in situ, and undergo clean hydrostannation to give a mixture of the regioisomeric aryl stannanes. The whole reaction sequence can also be carried out as a one-pot reaction under microwave irradiation. Georg Thieme Verlag Stuttgart New York.

Intermolecular N-heterocyclic carbene catalyzed hydroacylation of arynes

A formal introduction: The conceptually new N-heterocyclic carbene catalyzed formal insertion of arynes into the Cformyl-H bond of aldehydes demonstrates the compatibility of nucleophilic NHCs with electrophilic arynes. This NHC-catalyzed hydroacylation of arynes allows the conversion of aliphatic, α,β-unsaturated, and aromatic aldehydes into aryl ketones; 27 examples and a preliminary mechanistic investigation are provided. Copyright

An efficient procedure for the synthesis of ortho-trialkylsilylaryl triflates: Easy access to precursors of functionalized arynes

o-Trialkylsilylaryl triflates which are useful aryne precursors are prepared from o-bromophenols by an efficient, one-pot procedure involving O-silylation, metal-halogen exchange, O- to C-silyl migration, and entrapment of the phenoxide with triflic anhydride.

Selective palladium-catalyzed cocyclotrimerization of arynes with dimethyl acetylenedicarboxylate: A versatile method for the synthesis of polycyclic aromatic hydrocarbons

Benzyne (1a) and the substituted derivatives 4,5-difluorobenzyne (1b) and 3-methoxybenzyne (2) undergo chemoselective palladium-catalyzed [2 + 2 + 2]-cocyclotrimerization with dimethyl acetylenedicarboxylate (DMAD) to afford the corresponding phenanthrenes s and/or naphthalenes. The major products are phenanthrenes if Pd(PPh3)4 is used as the catalyst, naphthalenes if Pd2(dba)3 is used. When the method is applied to polycyclic arynes 3-6, which are generated from the corresponding o-trimethylsilylaryl triflates, the same reactivity pattern is observed: the reaction can be selectively directed either toward the cocyclization of one molecule of aryne and two molecules of alkyne or to the reaction of two molecules of aryne with one molecule of alkyne, by appropriate choice of the palladium catalyst. The synthesis of polycyclic aromatic compounds 33-39 using this methodology is reported.