17876-95-8

Basic information

• Product Name: Benzenemethanol, a-(trimethylsilyl)-
• CAS NO: 17876-95-8
• Molecular Formula: C10H16OSi
• Molecular Weight: 180.322
• Mol File: 17876-95-8.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: Benzenemethanol, a-(trimethylsilyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, a-(trimethylsilyl)-(17876-95-8)
• EPA Substance Registry System: Benzenemethanol, a-(trimethylsilyl)-(17876-95-8)

Safety Data

• Hazardous Substances Data: 17876-95-8(Hazardous Substances Data)

Usage

Common Uses

Organic Synthesis: Employed as a reagent for protecting alcohols and phenols in organic synthesis.
Protection of Hydroxyl Groups: The trimethylsilyl group safeguards hydroxyl groups from undesired reactions during chemical transformations.
Gas Chromatography-Mass Spectrometry (GC-MS) Analysis: Utilized as a derivatization reagent in GC-MS analysis to enhance the volatility and thermal stability of target analytes.
Potential Industrial Applications: Holds potential in pharmaceutical and agrochemical industries for synthesis purposes.

Versatile Reagent

Suitable for synthesizing various organic compounds due to its adaptable nature.

Upstream product

• 14642-79-6 benzyloxy-trimethylsilane 
• 75-77-4 chloro-trimethyl-silane 
• 93-99-2 benzoic acid phenyl ester 
• 5908-41-8 benzoyltrimethylsilane 
• 110-53-2 1-Bromopentane 
• 75-89-8 2,2,2-trifluoroethanol 
• 131123-35-8 α-Trimethylsilylbenzyl p-toluenesulfonate 
• 17903-41-2 phenyl(trimethylsilyl)methyl bromide 
• 75144-61-5 phenyl (trimethylsilyl)methyl ether 
• 7677-24-9 trimethylsilyl cyanide 
• 100-52-7 benzaldehyde 
• 126404-90-8 tert-Butyl-carbamic acid phenyl-trimethylsilanyl-methyl ester 
• 100-51-6 benzyl alcohol 
• 93-89-0 benzoic acid ethyl ester 

Downstream Products

• 53780-87-3 benzene 
• 66493-50-3 Benzyl-<α-(trimethylsilyl)-benzyl)>-ether 
• 250234-77-6 C₁₃H₁₈OSi 
• 250234-67-4 C₁₄H₂₂OSi 
• 250234-69-6 C₁₄H₂₂OSi 
• 250234-71-0 C₁₄H₂₂OSi 
• 14642-79-6 benzyloxy-trimethylsilane 
• 20453-83-2 trans-3,4-diphenyl-γ-butyrolactone 
• 134967-87-6 1-(methoxymethoxy)-1-phenylpentan-2-ol 
• 134968-14-2 3-(hydroxyphenylmethyl)cyclohexanone 
• 113249-10-8 3-<(methoxymethoxy)(phenyl)methyl>cyclohexanone 

Relevant articles and documents

N-Heterocyclic carbene-mediated organocatalytic transfer of tin onto aldehydes: New access to α-silyloxyalkylstannanes and γ- silyloxyallylstannanes

A new, highly efficient and mild N-heterocyclic carbene (NHC)-mediated organocatalytic procedure for the transfer of tin from tributyl(trimethylsilyl) stannane (Bu3SnSiMe3) onto aldehydes for the preparation of α-silyloxyalkylstannanes and γ-silyloxyallylstannanes has been developed.

-

-

Visible-Light Photoredox-Catalyzed Hydroalkoxymethylation of Activated Alkenes Using α-Silyl Ethers as Alkoxymethyl Radical Equivalents

A new neutral silicon-based traceless activation group (TAG) for visible-light photoredox-catalyzed hydroalkoxymethylation of alkenes is presented. This reaction involves in-situ-generated alkoxymethyl radical via single electron oxidation (SET) of α-TMS-substituted ethers, followed by subsequent conjugate addition to activated alkenes. Various functional groups were tolerated both under mild metal and metal-free conditions to provide good to excellent yields. Furthermore, the addition products were transformed to valuable synthetic building blocks, such as carboxylic acids,-butyrolactones, and complex aryl alkyl ethers.

Oxidative [1,2]-Brook Rearrangements Exploiting Single-Electron Transfer: Photoredox-Catalyzed Alkylations and Arylations

Oxidative [1,2]-Brook rearrangements via hypervalent silicon intermediates induced by photoredox-catalyzed single-electron transfer have been achieved, permitting the formation of reactive radical species that can engage in alkylations and arylations.