14642-79-6

Basic information

• Product Name: BENZYLOXYTRIMETHYLSILANE
• Synonyms: BENZYLOXYTRIMETHYLSILANE;Silane, (benzyloxy)trimethyl-;Silane, trimethyl(phenylmethoxy)-;BENZYLOXYTRIMETHYLSILANE 98%;Benzyl trimethylsilyl ether, Trimethylbenzyloxysilane;(Trimethylsiloxymethyl)benzene;Benzyl (trimethylsilyl) ether;Phenyl(trimethylsilyloxy)methane
• CAS NO: 14642-79-6
• Molecular Formula: C₁₀H₁₆OSi
• Molecular Weight: 180.32
• Mol File: 14642-79-6.mol
• Article Data: 167

Chemical Properties

• Boiling Point: 92 °C
• Flash Point: 73°C
• Appearance: Clear very pale yellow liquid
• Density: 0.916
• Vapor Pressure: 0.373mmHg at 25°C
• Refractive Index: 1.4770
• Solubility: Chloroform, Dichloromethane
• CAS DataBase Reference: BENZYLOXYTRIMETHYLSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYLOXYTRIMETHYLSILANE(14642-79-6)
• EPA Substance Registry System: BENZYLOXYTRIMETHYLSILANE(14642-79-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39-24/25-23
• TSCA: No
• Hazardous Substances Data: 14642-79-6(Hazardous Substances Data)

Usage

Description

BENZYLOXYTRIMETHYLSILANE is a clear, very pale yellow liquid that serves as an intermediate in the synthesis of various organic compounds. It is particularly used in the production of [Di(benzyloxy)methyl]benzene (D417965), which is a reagent in organic chemical synthesis, including the synthesis of O-benzyl protected anti aldols.

Uses

Used in Organic Chemical Synthesis:
BENZYLOXYTRIMETHYLSILANE is used as an intermediate for the synthesis of [Di(benzyloxy)methyl]benzene (D417965), which is an essential reagent in organic chemical synthesis. This application is crucial for the production of O-benzyl protected anti aldols, a type of compound with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, BENZYLOXYTRIMETHYLSILANE plays a significant role in the synthesis of complex organic molecules that can be used as active pharmaceutical ingredients or building blocks for drug development. Its ability to act as an intermediate in the production of D417965 makes it a valuable component in the creation of new and innovative medications.
Used in Chemical Research:
BENZYLOXYTRIMETHYLSILANE is also utilized in chemical research, where it can be employed to study the properties and reactions of various organic compounds. Its use in the synthesis of D417965 and other related compounds allows researchers to explore new avenues in chemical synthesis and potentially discover novel applications for these materials.

InChI:InChI=1/C10H16OSi/c1-12(2,3)11-9-10-7-5-4-6-8-10/h4-8H,9H2,1-3H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 100-51-6 benzyl alcohol 
• 538-86-3 benzyl methyl ether 
• 73296-31-8 phenyltellurotrimethylsilane 
• 100-52-7 benzaldehyde 
• 43112-38-5 3-(trimethylsilyl)-2-oxazolidinone 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 7677-24-9 trimethylsilyl cyanide 
• 4648-54-8 trimethylsilylazide 
• 762-72-1 allyl-trimethyl-silane 
• 993-07-7 trimethylsilan 
• 201230-82-2 carbon monoxide 
• 70582-00-2 1,1,1,3,3-pentamethyldisilazane 
• 18182-35-9 dimethyl(tert-butyl)aminosilane 

Downstream Products

• 124853-79-8 C₁₃H₁₈O₄Si 
• 67-64-1 acetone 
• 1000-49-3 n-butyltrimethylsilane 
• 143446-35-9 (E)-(2S)-Methyl 6-(benzyloxy)-2-methoxy-4-methyldec-3-enoate 
• 140-11-4 Benzyl acetate 
• 77903-22-1 1-Benzyl-2-benzoyl-1,3-dithiolanium triflate 
• 108461-98-9 2-(benzyloxy)cyclopent-2-enone 
• 22767-96-0 Benzyl 3-phenylpropionate 
• 143446-39-3 (E)-(2R,5S,6R)-Methyl 6,7-bis(benzyloxy)-2-methoxy-5-methylhept-3-enoate 
• 136174-58-8 (E)-(2R,5R,6S)-6,7-Bis-benzyloxy-2-methoxy-5-methyl-hept-3-enoic acid methyl ester 
• 146962-10-9 (E)-(2S,5S,6R)-Methyl 2-acetoxy-6,7-bis(benzyloxy)-5-methylhept-3-enoate 
• 3429-52-5 2,2,3-trimethyl-2-silabutane 
• 115140-08-4 (1RS,2RS)-5,5-bis(benzyloxy)-7-oxabicyclo<2.2.1>hept-2-ene 
• 54469-08-8 phenylmethyl 2,3:5,6-di-O-(1-methylethylidene)-α-D-mannofuranoside 

Relevant articles and documents

Comparison of the efficiency of two dicationic ionic liquids catalysts based on perchloric acid for the protection of alcohols

In this article, two aliphatic and aromatic types of dicationic acidic ionic liquids formulated as [H2-DABCO][ClO4], [H2-Bisim][ClO4]2 were used for the acceleration of the protection of alcohols as t

Counterattack Reagent Hexamethyldisilane in the Direct Conversion of Aldehydes, Ketones, and Allyl Alcohols to Allyltrimethylsilanes

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An asymmetric Salamo-based Zn complex supported on Fe3O4MNPs: a novel heterogeneous nanocatalyst for the silyl protection and deprotection of alcohols under mild conditions

In this study, a magnetic asymmetric Salamo-based Zn complex (H2L = salen type di-Schiff bases)-supported on the surface of modified Fe3O4(Fe3O4@H2L-Zn) as a new catalyst was designed and characterizedvianumerous analytical techniques such as FT-IR spectroscopy, XRD, EDS, ICP-AES, SEM, TEM, TGA and VSM. An efficient and sustainable synthetic protocol has been presented for the synthesis of silyl ether substructuresviathe silyl protection of alcohols under mild conditions. The synthetic protocol involves a two-component solvent-free reaction between various hydroxyl-bearing substrates and hexamethyldisilazane (HMDS) as an inexpensive silylating agent using Fe3O4@H2L-Zn MNPs as a magnetically separable, recyclable and reusable heterogeneous catalyst. Fe3O4@H2L-Zn MNPs were also applied for the removal of silyl protecting groups from hydroxyl functions using water in CH2Cl2under green conditions. The catalyst demonstrated good to excellent catalytic yield efficiency for both the reactions compared to the commercial metal-based catalysts under green conditions for a wide range of substrates.

Silylation of Alcohols, Phenols, and Silanols with Alkynylsilanes – an Efficient Route to Silyl Ethers and Unsymmetrical Siloxanes

The formation of several silyl ethers (alkoxysilanes, R3Si-OR') and unsymmetrical siloxanes (R3Si-O-SiR'3) can be catalyzed by the commercially available potassium bis(trimethylsilyl)amide (KHMDS). The reaction proceeds via direct dealkynative coupling between various alcohols or silanols and alkynylsilanes, with a simultaneous formation of gaseous acetylene as the sole by-product. The dehydrogenative and dealkenative coupling of alcohols or silanols are well-investigated, whilst the utilization of alkynylsilanes as silylating agents has never been comprehensively studied in this context. Overall, the presented system allows the synthesis of various attractive organosilicon compounds under mild conditions, making this approach an atom-efficient, environmentally benign, and sustainable alternative to existing synthetic solutions.