86605-93-8

Basic information

• Product Name: 4-bromo-α-(trimethylsilyl)toluene
• Synonyms: 4-bromo-α-(trimethylsilyl)toluene
• CAS NO: 86605-93-8
• Molecular Formula: C₁₀H₁₅BrOSi
• Molecular Weight: 259.215
• Mol File: 86605-93-8.mol
• Article Data: 43

Chemical Properties

• Melting Point: 26-29 °C(lit.)
• Flash Point: 110 °C
• Appearance: /
• Density: 1.190 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.531
• CAS DataBase Reference: 4-bromo-α-(trimethylsilyl)toluene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromo-α-(trimethylsilyl)toluene(86605-93-8)
• EPA Substance Registry System: 4-bromo-α-(trimethylsilyl)toluene(86605-93-8)

Safety Data

• Hazardous Substances Data: 86605-93-8(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 873-75-6 4-bromobenzenemethanol 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 130534-91-7 1-bromo-4-[(methoxymethyloxy)methyl]benzene 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 216443-67-3 4-bromo-1-[(ethoxymethoxy)methyl]benzene 
• 33861-17-5 phenyl trimethylsilyl selenide 
• 1122-91-4 4-bromo-benzaldehyde 

Downstream Products

• 873-75-6 4-bromobenzenemethanol 
• 21388-92-1 4-bromobenzyl acetate 
• 67627-98-9 p-bromo-α,α-dichlorotoluene 
• 25062-46-8 4-bromobenzaldehyde oxime 
• 2740-89-8 1-bromo-4-(thiocyanatomethyl)benzene 
• 51176-48-8 4-Propargylbenzyl alcohol 
• 146800-13-7 Tris(4-hydroxymethylphenyl)bismuthine 
• 1122-91-4 4-bromo-benzaldehyde 
• 55883-45-9 4-bromobenzyliodide 

Relevant articles and documents

SYNTHESIS STRATEGY FOR GAP PROTECTING GROUP

The present invention relates to a novel synthesis method to form particular molecules. These molecules have multiple uses, most notably in the field of protecting groups used throughout organic and synthetic chemistry. The disclosed method is safer, more

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.

Graphene oxide-bound electron-deficient tin(IV) porphyrin: a highly efficient and selective catalyst for trimethylsilylation of alcohols and phenols with hexamethyldisilazane

The catalytic activity of graphene oxide-bound tetrakis(p-aminophenyl)porphyrinatotin(IV) trifluoromethanesulfonate, [SnIV(TNH2PP)(OTf)2], in the trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) is reported. The prepared catalyst was characterized using inductively coupled plasma analysis, scanning electron microscopy, transmission electron microscopy, and Fourier transform infrared and diffuse reflectance UV–visible spectroscopies. This heterogeneous catalyst was used for selective trimethylsilylation of various alcohols and phenols with HMDS in short reaction times and high yields. Also, the catalyst is of high reusability and stability, in that it was recovered several times without loss of its initial activity. The chemoselectivity of this catalytic system in the silylation of primary alcohols in the presence of secondary and tertiary alcohols and also phenols was investigated.

Chlorozincate(II) acidic ionic liquid: Efficient and biodegradable silylation catalyst

A practical and highly efficient silylation of alcohol and phenol derivatives with hexamethyldisilazane (HMDS) using acidic ionic liquids under mild reaction conditions is described. A series of Br?nsted as well as Br?nsted–Lewis acidic ionic liquids were prepared and their performance investigated for the silylation of a wide variety of alcohols and phenols with HMDS. Imidazole- as well as N-methyl-2-pyrrolidone-based acidic ionic liquids have a higher catalytic activity for the protection of sensitive, hindered alcohols and phenols, thus providing an environmentally begin and versatile alternative to current acid catalysts. In addition, the acidic ionic liquids are reusable, being recovered easily and reused several times without significant deterioration in catalytic activity.

Room temperature silylation of alcohols catalyzed by metal organic frameworks

The commercial Al(OH)(BDC) (BDC: 1,4-benzenedicarboxylic acid) metal organic framework (Basolite A100) is a suitable heterogeneous catalyst for the silylation of benzylic and aliphatic alcohols by hexamethyldisilazane in toluene at room temperature. Al(OH

Introduction of PEG-SANM nanocomposite as a new and highly efficient reagent for the promotion of the silylation of alcohols and phenols and deprotection of the silyl ethers

Poly (ethylene glycol)-sulfonated sodium montmorillonite (PEG-SANM) nanocomposite was prepared by a simple method and characterized using XRD, TGA, SEM, TEM, and FT-IR techniques. After preparation and characterization, this reagent was used as a highly efficient and reusable solid acid catalyst for the chemoselective silylation of alcohols and phenols and deprotection of the obtained silyl ethers. Themethod offers several advantages including high to excellent yields of the products, short reaction times, easy preparation of the catalyst and easy work-up procedure. In addition, the catalyst can be recycled and reused at least for five times without significant decrease in the catalytic activity.

Preparation and characterization of a RHA/TiO2 nanocomposite: Introduction of an efficient and reusable catalyst for chemoselective trimethylsilyl protection and deprotection of alcohols and phenols

In this work, rice husk ash (RHA), as a natural source of amorphous silica, was used as a support for the synthesis of anatase-phase titania nanoparticles leading to the RHA/TiO2 nanocomposite. This nanocomposite was used as an efficient catalyst for the chemoselective trimethylsilylation of various alcohols and phenols and deprotection of the obtained trimethylsilyl ethers. The procedure gave the products in excellent yields in very short reaction times. Also this catalyst can be reused at least six times without loss of its catalytic activity.

RuIII(OTf)SalophenCH2-NHSiO2-Fe: An efficient and magnetically recoverable catalyst for trimethylsilylation of alcohols and phenols with hexamethyldisilazane

Efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) catalyzed by ruthenium(III) complex of chloromethylated Salophen supported on nanomagnetic materials is reported. First, the iron nanomagnets were silica coated, functi

Rice husk: Introduction of a green, cheap and reusable catalyst for the protection of alcohols, phenols, amines and thiols

A mild, efficient and eco-friendly protocol for the chemoselective protection of benzylic and primary and less hindered secondary aliphatic alcohols and phenols as trimethylsilyl ethers and different types of amines as N-tert-butylcarbamates is developed using rice husk (RiH) as the catalyst. This reagent is also able to catalyze the acetylation of alcohols, phenols, thiols and amines with acetic anhydride. Easy work-up, relatively short reaction times, excellent yields and low cost, availability and reusability of the catalyst are the striking features of this methodology, which can be considered to be one of the best and general methods for the protection of alcohols, phenols, thiols and amines. In addition, the use of a green reagent in the above-mentioned reactions results in a reduction of environmental pollution and of the cost of the applied methods.

Rice husk ash: A new, cheap, efficient, and reusable reagent for the protection of alcohols, phenols, amines, and thiols

Amild, efficient, and eco-friendly protocol for the protection of alcohols and phenols as trimethylsilyl ethers has been developed using rice husk ash as a reagent. This reagent is also able to catalyze the acetylation of alcohols, phenols, thiols, and amines with acetic anhydride. All reactions were performed under mild conditions in good to high yields. Copyright