556812-41-0

Basic information

• Product Name: 4-METHOXY-2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE
• Synonyms: 4-Methoxy-2-(trimethylsilyl)phenyl Triflate Trifluoromethanesulfonic Acid 4-Methoxy-2-(trimethylsilyl)phenyl Ester;Methanesulfonic acid, trifluoro-, 4-Methoxy-2-(triMethylsilyl)phenyl ester;4-METHOXY-2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE;4-METHOXY-2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE,95.0+%(GC);4-Methoxy-2-(trimethylsilyl)phenyl Triflate;Trifluoromethanesulfonic Acid 4-Methoxy-2-(trimethylsilyl)phenyl Ester
• CAS NO: 556812-41-0
• Molecular Formula: C11H15F3O3SSi
• Molecular Weight: 328.38
• Product Categories: Synthetic Organic Chemistry;Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Silicon Compounds (for Synthesis)
• Mol File: 556812-41-0.mol

Chemical Properties

• Boiling Point: 322.387°C at 760 mmHg
• Flash Point: 148.775°C
• Appearance: /
• Density: 1.25
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.4640 to 1.4680
• CAS DataBase Reference: 4-METHOXY-2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXY-2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE(556812-41-0)
• EPA Substance Registry System: 4-METHOXY-2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE(556812-41-0)

Safety Data

• Statements: 34
• Safety Statements: 36-62-26
• RIDADR: 3265
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 556812-41-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-METHOXY-2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE is used as a reagent for the protection and deprotection of functional groups in organic molecules. Its ability to facilitate various chemical reactions, such as the formation of carbon-carbon bonds and the introduction of new functional groups, makes it a versatile tool in organic synthesis.
Used in the Synthesis of Complex Molecules:
4-METHOXY-2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE is used as a reagent in the synthesis of complex molecules. Its trifluoromethanesulfonyl (triflate) group and trimethylsilyl group provide versatility and control in reactions, making it a valuable tool in the field of organic chemistry for the synthesis of complex molecules.

InChI:InChI=1/C11H15F3O4SSi/c1-17-8-5-6-9(10(7-8)20(2,3)4)18-19(15,16)11(12,13)14/h5-7H,1-4H3

Upstream product

• 1366440-80-3 4-methoxy-2-trimethylsilylphenyl methanesulfonate 
• 1366440-94-9 4-methoxy-2-trimethylsilylphenyl diethylphosphate 
• 17332-11-5 2-bromo-4-methoxyphenol 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 150-76-5 4-methoxy-phenol 
• 85630-29-1 4-methoxy-2-trimethylsilylphenol 
• 1004322-70-6 2-chloro-5-methoxyphenyltrimethylsilane 

Downstream Products

• 1004322-83-1 2-allyl-5-methoxyphenyltrimethylsilane 
• 1004322-78-4 2-(2,2,2-trifluoroethoxy)-5-methoxytrimethylsilylbenzene 
• 17876-90-3 3-trimethylsilylanisol 
• 1004322-81-9 4-methoxy-2-trimethylsilylbiphenyl 
• 944583-29-3 2-trimethylsilyl-4-methoxyacetanilide 
• 85630-29-1 4-methoxy-2-trimethylsilylphenol 

Relevant articles and documents

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Trifluoromethyl aryl sulfonates (TFMS): An applicable trifluoromethoxylation reagent

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

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Gold-catalyzed isomerization of unactivated allenes into 1,3-dienes under ambient conditions

We have developed a gold-catalyzed isomerization of unactivated allenes into 1,3-dienes with nitrosobenzene as an additive. This reaction proceeded almost exclusively at room temperature for highly substituted allenes. The utility of this reaction is manifested by the development of one-pot [4+2]-cycloaddition of allenes and reactive alkenes.

Probing for a leaving group effect on the generation and reactivity of phenyl cations

Phenyl cations are smoothly generated by the photoheterolytic cleavage of an Ar-LG bond (LG = leaving group). With the aim of evaluating the scope of the method, a series of 4-methoxy-2-(trimethylsilyl)phenyl derivatives (sulfonic, LG = MeSO3 and CF3SO3, phosphate, LG = (EtO) 2(O)PO esters and the corresponding chloride) have been compared as probes for evaluating the leaving group ability. The photocleavage was a general reaction, with the somewhat surprising order (EtO)2(O)PO ～ Cl > CF3SO3 > MeSO3 (φ = 0.50 to 0.16 in CF3CH2OH and lower values in MeCN-H2O). The ensuing reactions did not depend on the LGs but only on the structure of the phenyl cation (the silyl group tuned the triplet to singlet intersystem crossing and the electrophilicity) and on the medium (formation of a complex with water slowed the electrophilic reactions).

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.