57754-01-5

Basic information

• Product Name: 2-[(Trimethylsilyl)methyl]benzenemethanol
• Synonyms: 2-(Trimethylsilylmethyl)benzyl alcohol;2-[(Trimethylsilyl)methyl]benzenemethanol;(2-((Trimethylsilyl)methyl)phenyl)methanol
• CAS NO: 57754-01-5
• Molecular Formula: C₁₁H₁₈OSi
• Molecular Weight: 194.35
• Mol File: 57754-01-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-[(Trimethylsilyl)methyl]benzenemethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(Trimethylsilyl)methyl]benzenemethanol(57754-01-5)
• EPA Substance Registry System: 2-[(Trimethylsilyl)methyl]benzenemethanol(57754-01-5)

Safety Data

• Hazardous Substances Data: 57754-01-5(Hazardous Substances Data)

Usage

Physical state

Clear, colorless liquid

Functional group

Trimethylsilyl group attached to the methyl carbon

Use as a protecting group

Commonly used in organic synthesis to protect alcohols during chemical reactions, allowing for selective manipulation of functional groups and preventing unwanted reactions

Use as a reagent

Utilized in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds.

Upstream product

• 71435-93-3 o-<(trimethylsilyl)methyl>benzoic acid 
• 83781-92-4 o-[(trimethylsilyl)methyl]benzyl trimethylsilyl ether 
• 89-95-2 2-methyl-benzyl alcohol 
• 529-20-4 2-methylphenyl aldehyde 

Downstream Products

• 81522-28-3 o-<(trimethylsilyl)methyl>benzaldehyde 
• 83781-93-5 o-((trimethylsilyl)methyl)benzyl chloride 
• 104330-78-1 2-(trimethylsilylmethyl)benzyl bromide 
• 240802-24-8 C₁₇H₂₂SSi 
• 857802-75-6 (2SR,3SR)-2-acetyl-3-phenyl-1,2,3,4-tetrahydronaphthalene 
• 29422-13-7 2-phenyltetralin 
• 34599-77-4 (E)-1-methyl-2-(penta-2,4-dien-2-yl)benzene 
• 82902-64-5 (E)-1-(but-2-en-2-yl)-2-methylbenzene 
• 134261-82-8 1-Methyl-2-(1-methylene-but-3-enyl)-benzene 
• 82902-62-3 2-(2-methylphenyl)but-1-ene 
• 83845-46-9 1-Methyl-2-(1-methylene-hex-5-enyl)-benzene 
• 160929-85-1 Trimethyl-{2-[1-methyl-1-(toluene-4-sulfonyl)-propyl]-benzyl}-silane 
• 160929-86-2 {2-[1-Ethyl-1-(toluene-4-sulfonyl)-propyl]-benzyl}-trimethyl-silane 

Relevant articles and documents

Synthesis and Conversions of Substituted o-[(Trimethylsilyl)methyl]benzyl p-Tolyl Sulfones to o-Quinodimethanes and Products Thereof

Use of o-[(trimethylsilyl)methyl]benzyl p-tolyl sulfone (3) for synthesis and cycloaddition of substituted o-quinodimethanes has been investigated. Sulfone 3 is prepared from 2-methylbenzyl alcohol (4) by reactions with n-BuLi and chlorotrimethylsilane to form o-[(trimethylsilyl)methyl]-benzyl alcohol (7) which phosphorus tribromide converts to o-[(trimethylsilyl)methyl]benzyl bromide (8). Displacement of 8 with sodium p-toluenesulfinate yields 3. Sulfone 3 is alkylated at its α-sulfonyl position upon deprotonation with n-BuLi followed by methyl iodide, ethyl, butyl, allyl, and benzyl bromides, and 5-bromo-1-pentene, respectively. Acylations occur using acid chlorides. Dialkylation occurs upon further reaction with n-BuLi and an alkyl halide. 1,4-Eliminations of α,α-dialkyl sulfones 11 with tetrabutylammonium fluoride (TBAF) give α,α-dialkyl-o-quinodimethanes (29); 3 is therefore a synthon for the o-quinodimethane-α,α-dianion (34). o-Quinodimethanes 29 undergo (1) cycloaddition with acrylonitrile, acrylate esters, and alkyl fumarates to yield 1,1-disubstituted-tetrahydronaphthalenes (30) and (2) 1,5-sigmatropic rear-rangements of hydrogen to give styrenes (32). The stereochemistries of the various cycloadditions reveal significant mechanism information.

DIRADICAL CYCLIZATION METHODOLOGIES. MODEL STUDIES PROBING THE APPLICATION OF PHOTOINDUCED-ELECTRON TRANSFER PROCESSES IN SYNTHETIC ROUTES TO THE PROTOBERBERINE AND SPIROBENZYL ISOQUINOLINE ALKALOIDS

Model studies have demonstrated that diradical cyclization processes, promoted by excited state electron transfer-desilylation pathways, serve as novel methods for construction of ring systems found in members of the protoberberine and spirobenzyl isoquin