1009-02-5

Basic information

• Product Name: 2-Methylphenyl(trimethylsilyl) ether
• Synonyms: 1-(Trimethylsiloxy)-2-methylbenzene;2-Methylphenyl(trimethylsilyl) ether;Trimethyl(2-methylphenoxy)silane
• CAS NO: 1009-02-5
• Molecular Formula: C₁₀H₁₆OSi
• Molecular Weight: 180.32
• Mol File: 1009-02-5.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 195.4°C at 760 mmHg
• Flash Point: 64°C
• Appearance: /
• Density: 0.908g/cm³
• Vapor Pressure: 0.588mmHg at 25°C
• Refractive Index: 1.473
• CAS DataBase Reference: 2-Methylphenyl(trimethylsilyl) ether(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylphenyl(trimethylsilyl) ether(1009-02-5)
• EPA Substance Registry System: 2-Methylphenyl(trimethylsilyl) ether(1009-02-5)

Safety Data

• Hazardous Substances Data: 1009-02-5(Hazardous Substances Data)

Usage

General Description

2-Methylphenyl(trimethylsilyl) ether is an organic compound consisting of a phenyl group with a methyl substituent and a trimethylsilyl group attached to the oxygen atom. It is commonly used as a protecting group in organic synthesis to block the reactivity of hydroxyl groups in molecules. The trimethylsilyl group acts as a temporary shield, allowing for selective reactions to take place without affecting the hydroxyl groups. 2-Methylphenyl(trimethylsilyl) ether is also used as a precursor in the synthesis of various organic compounds and pharmaceuticals due to its stability and ease of removal under mild conditions.

InChI:InChI=1/C10H16OSi/c1-9-7-5-6-8-10(9)11-12(2,3)4/h5-8H,1-4H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 95-48-7 ortho-cresol 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 589-18-4 4-Methylbenzyl alcohol 
• 24589-78-4 N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide 
• 108-88-3 toluene 
• 25561-30-2 N,O-Bis(trimethylsilyl)trifluoroacetamide 
• 95-53-4 o-toluidine 
• 5796-98-5 bis-trimethylsilanyl peroxide 
• 6699-93-0 (2-methylphenyl)lithium 
• 95-46-5 2-methylphenyl bromide 
• 932-31-0 ortho-tolylmagnesium bromide 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 

Downstream Products

• 75-77-4 chloro-trimethyl-silane 
• 78083-57-5 3-methyl-4-hydroxyphenyltellurium trichloride 
• 95-48-7 ortho-cresol 
• 444575-93-3 (R)-(-)-1-phenyl-1-(2-methylphenoxy)-2-propene 

Relevant articles and documents

Gas-phase photocatalytic degradation and detoxification of o-toluidine: Degradation mechanism and Salmonella mutagenicity assessment of mixed gaseous intermediates

The photocatalytic degradation of toluidine over titanium oxide (TiO 2) thin films under UV irradiation was investigated. The degradation efficiency of 98.7% was obtained for a toluidine concentration of about 4500 μg L-1 and illumination of 240 min. The degradation intermediates produced during photocatalytic oxidation were identified using Fourier transform-infrared spectrometry (FTIR) and gas chromatography-mass spectrometry (GC-MS). Only a small amount of intermediates, including phenol and toluene, were found in the gas phase. Many other trace amount intermediates, such as 2-hydroxybenzaldehyde, 2-nitrobenzaldehyde, 2-hydroxybenzenemethanol, 2-hydroxybenzoic acid, phenol etc., were detected on the TiO2 surface. An Ames assay of the Salmonella typhimurium strains TA98 and TA100 was employed to evaluate the mutagenicity of toluidine and its gaseous photocatalytic degradation intermediates. With or without rat liver microsomal fraction (S9 mix) activation, neither toluidine nor its gaseous intermediates presented mutagenic activity against strains TA98 (±S9) and TA100 (-S9) at all tested doses. Toluidine, however, can induce a weak positive response to the TA100 strain with an S9 mix at doses as high as 4000 μg plate -1. An increase of revertants per plate was obtained after 30 min photocatalysis in the TA100 strain with S9 mix. As reaction time further increased, photocatalytic technology exhibited the ability to completely and efficiently detoxify toluidine. Both our chemical analysis and toxic evaluation indicate that all mutagenic intermediates in the gas can be completely eliminated within 240 min, which further suggests that photocatalytic technology is an effective approach for degrading aromatic amines.

An efficient method for the protection of alcohols and phenols by using hexamethyldisilazane in the presence of cupric sulfate pentahydrate under neutral reaction conditions

Alcohols and phenols are protected with hexamethyldisilazane in the presence of cupric sulfate pentahydrate in good to excellent yields in acetonitrile. The method is highly selective for the conversion of primary alcohols in the presence of secondary and tertiary alcohols as well as phenols. Georg Thieme Verlag Stuttgart.

Rapid and highly efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalyzed by reusable zirconyl triflate, [ZrO(OTf)2]

In this paper, rapid and efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane in the presence of catalytic amounts of ZrO(OTf)2 is reported. Primary, secondary and tertiary alcohols as well as phenols were efficiently converted to their corresponding TMS ethers in short reaction times at room temperature. It is noteworthy that this method can be used for chemoselective silylation of primary alcohols in the presence of secondary and tertiary alcohols and phenols.

A new and efficient method for the protection of alcohols and phenols by using hexamethyldisilazane in the presence of anhydrous ferric chloride under mild reaction conditions

Alcohols and phenols are protected with hexamethyldisilazane in the presence of anhydrous ferric chloride in good to excellent yields in acetonitrile. This method is highly selective for the conversion of primary alcohols in the presence of secondary and

Electrophilic Hydroxylation with Bis(trimethylsilyl)peroxide. A Synthon for the Hydroxyl Cation

The regiospecific introduction of an hydroxy group in aromatic and aliphatic compounds can be performed in good yields by electrophilic hydroxylation of their organometallic derivatives with bis(trimethylsilyl)peroxide.

Nanoporous Na+-montmorillonite perchloric acid as an efficient and recyclable catalyst for the chemoselective protection of hydroxyl groups

Nanoporous Na+-montmorillonite perchloric acid as a novel heterogeneous reusable solid acid catalyst was easily prepared by treatment of Na+-montmorillonite as a cheap and commercially available support with perchloric acid. The catalyst was characterized using a variety of techniques including X-ray powder diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), thermogravimetric analysis (TGA), energy dispersive X-ray spectroscopy (EDX), pH analysis and determination of the Hammett acidity function. The prepared reagent showed excellent catalytic activity for the chemoselective conversion of alcohols and phenols to their corresponding trimethylsilyl ethers with 1,1,1,3,3,3-hexamethyldisilazane (HMDS) at room temperature. Deprotection of the resulting trimethylsilyl ethers can also be carried out using the same catalyst in ethanol. All reactions were performed under mild and completely heterogeneous reaction conditions in good to excellent yields. The notable advantages of this protocol are: short reaction times, high yields, availability and low cost of the reagent, easy work-up procedure and the reusability of the catalyst during a simple filtration.

Nanomagnetic zirconia-based sulfonic acid (Fe3O4@ZrO2-Pr-SO3H): A new, efficient and recyclable solid acid catalyst for the protection of alcohols: Via HMDS under solvent free conditions

In the present work, sulfonic acid functionalized nanomagnetic zirconia is prepared by the reaction of (3-mercaptopropyl)trimethoxysilane and nanomagnetic zirconia. Then, nanomagnetic zirconia-based sulfonic acid (Fe3O4@ZrO2/su