22515-30-6

Basic information

• Product Name: Benzoic acid, 4-(trimethylsilyl)-, methyl ester
• CAS NO: 22515-30-6
• Molecular Formula: C11H16O2Si
• Molecular Weight: 208.332
• Mol File: 22515-30-6.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 4-(trimethylsilyl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-(trimethylsilyl)-, methyl ester(22515-30-6)
• EPA Substance Registry System: Benzoic acid, 4-(trimethylsilyl)-, methyl ester(22515-30-6)

Safety Data

• Hazardous Substances Data: 22515-30-6(Hazardous Substances Data)

Upstream product

• 6999-03-7 1-bromo-4-(trimethylsilyl)benzene 
• 616-38-6 carbonic acid dimethyl ester 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 574755-28-5 (4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)trimethylsilane 
• 74-88-4 methyl iodide 
• 75748-12-8 methyl 4‐(2,2,2‐trifluoroacetyl)benzoate 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 619-44-3 methyl 4-iodobenzoate 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 79-22-1 methyl chloroformate 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 1129-35-7 4-cyanobenzoic acid methyl ester 

Downstream Products

• 792-74-5 4,4'-biphenyldicarboxylic acid dimethyl ester 
• 145208-53-3 methyl 4-(5-bromothiophen-2-yl)benzoate 
• 1234714-99-8 C₂₂H₂₃NO₅ 
• 128982-09-2 5-(4-Trimethylsilanyl-phenyl)-2,3,5,6-tetrahydro-imidazo[2,1-a]isoquinolin-5-ol 

Relevant articles and documents

Design, Synthesis, and Implementation of Sodium Silylsilanolates as Silyl Transfer Reagents

There is an increasing demand for facile delivery of silyl groups onto organic bioactive molecules. One of the common methods of silylation via a transition-metal-catalyzed coupling reaction employs hydrosilane, disilane, and silylborane as major silicon sources. However, the labile nature of the reagents or harsh reaction conditions sometimes render them inadequate for the purpose. Thus, a more versatile alternative source of silyl groups has been desired. We hereby report a design, synthesis, and implementation of storable sodium silylsilanolates that can be used for the silylation of aryl halides and pseudohalides in the presence of a palladium catalyst. The developed method allows a late-stage functionalization of polyfunctionalized compounds with a variety of silyl groups. Mechanistic studies indicate that (1) a nucleophilic silanolate attacks a palladium center to afford a silylsilanolate-coordinated arylpalladium intermediate and (2) a polymeric cluster of silanolate species assists in the intramolecular migration of silyl groups, which would promote an efficient transmetalation.

Nickel-Catalyzed Decarbonylation of Acylsilanes

Nickel-catalyzed decarbonylation of acylsilanes is developed. In sharp contrast to cross-coupling reactions of acylsilanes, in which the silyl group serves as a leaving group, the silyl group is retained in the product in this decarbonylation reaction. Although the strong binding of the dissociated CO to the nickel center frequently hinders catalyst turnover in nickel-mediated decarbonylative reactions, this reaction can be catalyzed by nickel complexes bearing a CO ligand.

Silylarene Hydrogenation: A Strategic Approach that Enables Direct Access to Versatile Silylated Saturated Carbo- and Heterocycles

We report a method to convert readily available silylated arenes into silylated saturated carbo- and heterocycles by arene hydrogenation. The scope includes alkoxy- and halosilyl substituents. Silyl groups can be derivatized into a plethora of functionalities and find application in organic synthesis, materials science, and pharmaceutical, agrochemical, and fragrance research. However, silylated saturated (hetero-) cycles are difficult to access with current technologies. The yield of the hydrogenation depends on the amount of the silica gel additive. This silica effect also enables a significant improvement of a previously disclosed method for the hydrogenation of highly fluorinated arenes (e.g., to all-cis-C6H6F6).