2-(Trimethylsilyl)phenyl trifluoromethanesulfonate

Base Information

• Chemical Name: 2-(Trimethylsilyl)phenyl trifluoromethanesulfonate
• CAS No.: 88284-48-4
• Molecular Formula: C10H13F3O3SSi
• Molecular Weight: 298.358
• Hs Code.: 29319090
• European Community (EC) Number: 629-383-8
• DSSTox Substance ID: DTXSID00391985
• Nikkaji Number: J1.151.519C
• Wikidata: Q72514542
• Mol file: 88284-48-4.mol

Synonyms:2-(Trimethylsilyl)phenyl trifluoromethanesulfonate;88284-48-4;2-(Trimethylsilyl)phenyl Triflate;(2-trimethylsilylphenyl) trifluoromethanesulfonate;2-(Trimethylsilyl)phenyltrifluoromethanesulfonate;MFCD00799598;Methanesulfonic acid, trifluoro-, 2-(trimethylsilyl)phenyl ester;C10H13F3O3SSi;(TRIMETHYLSILYL)PHENYL TRIFLATE;SCHEMBL1713611;DTXSID00391985;BCP10118;AKOS015856668;CS-W007378;DS-16426;SY057456;FT-0647471;T2089;A22396;2-(trimethylsilyl)phenyl trifluoromethane-sulfona;2-(Trimethylsilyl)phenol trifluoromethanesulfonate;2-(trimethylsilyl)phenyl trifluoromethane sulfonate;2-(trimethylsilyl)phenyl trifluoro-methane sulfonate;2-(Trimethylsilyl)phenyl trifluoromethanesulfonate, 97%;Trifluoromethanesulfonic Acid 2-(Trimethylsilyl)phenyl Ester;(3-BOC-AMINO-AZETIDIN-1-YL)-PYRIDIN-3-YL-ACETICACID

Chemical Property of 2-(Trimethylsilyl)phenyl trifluoromethanesulfonate

Chemical Property:

• Refractive Index: n20/D 1.456(lit.)
• Boiling Point: 70 °C2 mm Hg(lit.)
• Flash Point: 205 °F
• PSA: 51.75000
• Density: 1.229 g/mL at 25 °C(lit.)
• LogP: 3.54100
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 298.03067647
• Heavy Atom Count: 18
• Complexity: 381

Purity/Quality:

97%min ^*data from raw suppliers

2-(Trimethylsilyl)phenyl Trifluoromethanesulfonate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C1=CC=CC=C1OS(=O)(=O)C(F)(F)F
• Physical properties: bp 70 °C/2 mmHg; d 1.229 g mL?1
• Uses: 2-(Trimethylsilyl)phenyl Triflate is a useful reagent applied in reactions of Polycyclic Arenes, Heteroatom Arylation,Heteroarenes and Benzannulated Heterocycles, Carbon Arylations, etc. 2-(Trimethylsilyl)phenyl trifluoromethanesulfonate may be used to generate benzyne under mild conditions of simple fluoride treatment at room temperature.

Technology Process of 2-(Trimethylsilyl)phenyl trifluoromethanesulfonate

There total 11 articles about 2-(Trimethylsilyl)phenyl trifluoromethanesulfonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

trifluoromethylsulfonic anhydride (358-23-6) + 2-bromophenyl trimethylsilyl ether (36601-47-5) → 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4)

Guidance literature:

2-bromophenyl trimethylsilyl ether; With n-butyllithium; In diethyl ether; at 20 ℃; for 0.0166667h; Flow reactor;

trifluoromethylsulfonic anhydride; In diethyl ether; at 20 ℃; for 0.00202778h; Flow reactor;

DOI:10.1021/ol500959e

Reference yield: 90.0%

trifluoromethylsulfonic anhydride (358-23-6) + o-(trimethylsilyl)phenol (15288-53-6) → 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; Inert atmosphere;

DOI:10.1055/s-0029-1218631

Reference yield: 80.0%

trifluoromethylsulfonic anhydride (358-23-6) + 2-hydroxybromobenzene (95-56-7) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4)

Guidance literature:

2-hydroxybromobenzene; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; Reflux;

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

trifluoromethylsulfonic anhydride; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h;

DOI:10.1021/acs.orglett.1c02702

upstream raw materials:

trifluoromethylsulfonic anhydride

o-(trimethylsilyl)phenol trimethylsilyl ether

2-bromophenyl trimethylsilyl ether

N,N-phenylbistrifluoromethane-sulfonimide

Downstream raw materials:

9-ethyl-10-phenylphenanthrene

9-benzyl-phenanthrene

9-methyl-10-phenylphenanthrene

bis(p-methoxyphenyl)methanone

Refernces

• 1、 Li, Yang,Shi, Jiarong,Zhao, Jinlong. "Benzyne-Mediated Esterification Reaction". supporting information. p. 7274 - 7278. Retrieved 2021/10/01.
• 2、 Hsu, Ting-Wei,Kim, Cheoljae,Michaudel, Quentin. "Stereoretentive Ring-Opening Metathesis Polymerization to Access All- cis Poly(p-phenylenevinylene)s with Living Characteristics". supporting information. p. 11983 - 11987. Retrieved 2020/08/06.