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

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

• 17888-55-0 p-Trimethylsilylbenzoylchlorid 
• 124-41-4 sodium methylate 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 1112-54-5 vinyltriethylsilane 
• 1129-35-7 4-cyanobenzoic acid methyl ester 
• 24858-02-4 vinyl(tert-butyl)dimethylsilane 
• 121675-48-7 1-triisopropylsilyl-1-ethene 
• 754-05-2 ethenyltrimethylsilane 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 619-44-3 methyl 4-iodobenzoate 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 6999-03-7 1-bromo-4-(trimethylsilyl)benzene 

Downstream Products

• 1234714-99-8 C₂₂H₂₃NO₅ 
• 145208-53-3 methyl 4-(5-bromothiophen-2-yl)benzoate 
• 792-74-5 4,4'-biphenyldicarboxylic acid dimethyl ester 
• 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.

Mild Copper-Catalyzed Addition of Arylboronic Esters to Di- tert -butyl Dicarbonate: An Easy Access to Methyl Arylcarboxylates

An efficient copper-catalyzed addition of arylboronic esters to (Boc) 2O was developed. The reaction can be conducted under exceedingly mild conditions and is compatible with a variety of synthetically relevant functional groups. It therefore represents a useful alternative route for the synthesis of methyl arylcarboxylates. A preliminary mechanistic study indicated the involvement of an addition-elimination mechanism.

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.

Dimethylformamide-stabilised palladium nanoclusters catalysed coupling reactions of aryl halides with hydrosilanes/disilanes

N,N-Dimethylformamide-stabilised Pd nanocluster (NC) catalysed cross-coupling reactions of hydrosilane/disilane have been investigated. In this reaction, the coupling reaction proceeds without ligands with low catalyst loading. N,N-Dimethylacetamide is a crucial solvent in these reactions. The solvent effect was considered by various techniques, such as transmission electron microscopy, X-ray photoelectron spectroscopy, and thermogravimetric analysis. The Pd NCs can be recycled five times under both hydrosilane and disilane reaction conditions.

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).

Rhodium-catalyzed alkenylation of nitriles via silicon-assisted C-CN bond cleavage

Rhodium-catalyzed Mizoroki-Heck type reaction of nitriles via the cleavage of C-C bonds is described. Orthogonal and iterative functionalizations of arenes were also demonstrated by combining the present and conventional halide-based cross-coupling reacti

Gold-catalyzed oxidative coupling reactions with aryltrimethylsilanes

During continuing studies with a novel oxidative gold oxyarylation reaction, arylsilanes were found to be competent coupling partners, providing further evidence for an intramolecular electrophilic aromatic substitution mechanism. While providing yields complementary to those of the previously described boronic acid methods, the use of trimethylsilanes reduces the observation of homocoupling byproducts and allows for facile intramolecular coupling reactions.

A flow microreactor system enables organolithium reactions without protecting alkoxycarbonyl groups

A flow microreactor system consisting of micromixers and microtube reactors provides an effective tool for the generation and reactions of aryllithiums bearing an alkoxycarbonyl group at para-, meta-, and ortho-positions. Alkyl p- and m-lithiobenzoates were generated by the I/Li exchange reaction with PhLi. The Br/Li exchange reactions with sBuLi were unsuccessful. Subsequent reactions of the resulting aryllithiums with electrophiles gave the desired products in good yields. On the other hand, alkyl o-lithiobenzoates were successfully generated by the Br/ Li exchange reaction with sBuLi. Subsequent reactions with electrophiles gave the desired products in good yields.

Palladium-catalyzed silylation of aryl chlorides with hexamethyldisilane

A method for the palladium-catalyzed silylation of aryl chlorides has been developed. The method affords desired product in good yield, is tolerant of a variety of functional groups, and provides access to a wide variety of aryltrimethylsilanes from commercially available aryl chlorides. Additionally, a one-pot procedure that converts aryl chlorides into aryl iodides has been developed.

A practical preparation of methyl 4-(trimethylsilyl)benzoate: An intermediate in the synthesis of SDZ 63135

An improved synthesis of ester 1 is described utilizing a bromine-lithium exchange and a Grignard-mediated methoxycarbonylation reaction starting from 1,4-dibromobenzene. Compound 1 was converted to 2 through a condensation and dehydration sequence with an overall yield of 41.5%.