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 
• 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 
• 762-72-1 allyl-trimethyl-silane 
• 80384-83-4 Z-1-morpholino-2-trimethylsilyl-3-phenylpropene 
• 84355-13-5 N-Trimethylsilylpyridinium trifluoromethanesulfonate 
• 70582-00-2 1,1,1,3,3-pentamethyldisilazane 

Downstream Products

• 29624-04-2 benzenesulfinic acid benzyl ester 
• 1071205-57-6 α-Triaethylsiloxy-α-trimethylsilyltoluol 
• 35896-44-7 Benzyl-methansulfinat 
• 77966-19-9 1-Benzyl-2-(carboethoxy)-1,3-dithiolanium triflate 
• 140-11-4 Benzyl acetate 
• 77903-20-9 Trifluoro-methanesulfonateallyl-benzyl-ethoxycarbonylmethyl-sulfonium; 
• 120-51-4 benzoic acid benzyl ester 
• 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 

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.