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

Chemical Properties

Clear very pale yellow liquid

Uses

Benzyloxytrimethylsilane is an intermediate in the synthesis of [Di(benzyloxy)methyl]benzene (D417965), which is a reagent in organic chemical synthesis such as the synthesis of O-benzyl protected anti aldols.

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 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 107-46-0 Hexamethyldisiloxane 
• 538-86-3 benzyl methyl ether 
• 73296-31-8 phenyltellurotrimethylsilane 
• 16029-98-4 trimethylsilyl iodide 
• 2749-70-4 bis(benzyloxy)methane 
• 931-56-6 2-methoxycyclohexane 
• 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 

Downstream Products

• 53172-92-2 α-trimethylsilyl-α-trimethylsiloxytoluene 
• 1071205-57-6 α-Triaethylsiloxy-α-trimethylsilyltoluol 
• 35896-44-7 Benzyl-methansulfinat 
• 3358-25-6 Benzyl-(toluol-α-sulfinat) 
• 17876-95-8 (trimethylsilyl)phenylmethanol 
• 124853-79-8 C₁₃H₁₈O₄Si 
• 67-64-1 acetone 
• 77966-19-9 1-Benzyl-2-(carboethoxy)-1,3-dithiolanium triflate 
• 1000-49-3 n-butyltrimethylsilane 
• 143446-35-9 (E)-(2S)-Methyl 6-(benzyloxy)-2-methoxy-4-methyldec-3-enoate 
• 140-11-4 Benzyl acetate 
• 50741-71-4 2-benzyloxy-cyclohex-2-en-1-one 
• 120-51-4 benzoic acid benzyl ester 
• 108461-98-9 2-(benzyloxy)cyclopent-2-enone 

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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KF/clinoptilolite NPs: An efficient and heterogeneous catalyst for chemoselective silylation of alcohols and phenols

Potassium fluoride incorporated on clinoptilolite nanoparticles (KF/CP NPs) by ion exchanging is found to be an effective and inexpensive heterogeneous nanocatalyst for chemoselective silylation of alcohols and phenols with 1,1,1,3,3,3-hexamethyldisilazane (HMDS) at room temperature. Nano-powder of clinoptilolite (CP) was prepared using a planetary ball mill mechanically method and characterized by dynamic light scattering (DLS), X-ray powder diffraction (XRD) and scanning electron microscope (SEM) analyses. Almost all of products were obtained in high yields as well as short reaction times and the catalyst was also reused eight times without loss of its catalytic activity.

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.