17095-20-4

Basic information

• Product Name: (4-BROMOBENZYL)TRIMETHYLSILANE
• Synonyms: (4-BROMOBENZYL)TRIMETHYLSILANE;4-BROMO-ALPHA-(TRIMETHYLSILYL)TOLUENE;(4-bromophenyl)methyl-trimethylsilane
• CAS NO: 17095-20-4
• Molecular Formula: C₁₀H₁₅BrSi
• Molecular Weight: 243.22
• Mol File: 17095-20-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 26-29 °C(lit.)
• Boiling Point: 244.7°C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.190 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0467mmHg at 25°C
• Refractive Index: n20/D 1.531
• BRN: 774733
• CAS DataBase Reference: (4-BROMOBENZYL)TRIMETHYLSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: (4-BROMOBENZYL)TRIMETHYLSILANE(17095-20-4)
• EPA Substance Registry System: (4-BROMOBENZYL)TRIMETHYLSILANE(17095-20-4)

Safety Data

• WGK Germany: 3
• F: 8
• Hazardous Substances Data: 17095-20-4(Hazardous Substances Data)

Usage

General Description

(4-Bromobenzyl)trimethylsilane is an organosilicon compound with the molecular formula C10H13BrSi. It is a colorless liquid that is commonly used as a reagent in organic synthesis. The presence of a trimethylsilyl group attached to a bromobenzene ring makes this compound useful for various reactions, including nucleophilic substitution and cross-coupling reactions. It is also employed as a protecting group for alcohols and a precursor for the synthesis of various organic compounds. Additionally, (4-Bromobenzyl)trimethylsilane has applications in the field of materials science and is utilized in the preparation of silicon-containing polymers and functional materials.

InChI:InChI=1/C10H15BrSi/c1-12(2,3)8-9-4-6-10(11)7-5-9/h4-7H,8H2,1-3H3

Upstream product

• 770-09-2 benzyltrimethylsilane 
• 108-88-3 toluene 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 75-77-4 chloro-trimethyl-silane 
• 92206-72-9 4-bromobenzylmagnesium bromide 

Downstream Products

• 109088-72-4 Oxo-(4-trimethylsilanylmethyl-phenyl)-acetic acid ethyl ester 
• 67205-74-7 2-(4-bromophenyl)-1-(4-methoxyphenyl)ethan-1-ol 
• 1445712-97-9 (E)-1-(4-bromophenyl)-4-phenylbut-3-en-2-ol 
• 1178285-31-8 1-(4-bromophenyl)-4-phenylbutan-2-ol 
• 1612231-49-8 N-(2-(4-bromophenyl)-1-phenylethyl)-4-methoxyaniline 
• 1179121-88-0 1-(4-bromophenyl)-3,3-dimethylbutan-2-ol 
• 76284-87-2 2-(4-bromobenzyl)benzo[d]oxazole 
• 109088-55-3 p-<(trimethylsilyl)methyl>benzaldehyde <(triisopropylphenyl)sulfonyl>hydrazone 
• 109088-66-6 2-Isopropylidene-1-(4-trimethylsilanylmethyl-phenyl)-cyclopropanecarboxylic acid ethyl ester 
• 109088-65-5 2,2-Dimethyl-3-methylene-1-(4-trimethylsilanylmethyl-phenyl)-cyclopropanecarboxylic acid ethyl ester 
• 109088-57-5 [4-(2-Isopropylidene-cyclopropyl)-benzyl]-trimethyl-silane 
• 109088-46-2 [4-(2,2-Dimethyl-3-methylene-cyclopropyl)-benzyl]-trimethyl-silane 
• 109088-56-4 phenyldiazomethane 
• 145866-31-5 [4-(1,4-Dicyano-1,2-dihydro-naphthalen-1-ylmethyl)-phenyl]-acetic acid 

Relevant articles and documents

Synthesis and application of benzyl-TMS derivatives as bench stable benzyl anion equivalents

The regioselective benzylic metalation of toluenes using BuLi/KO tBu/TMP(H) (LiNK metalation conditions) and subsequent transmetalation to Si by reaction with TMSCl provides a general one-pot procedure for the synthesis of substituted benzyltrimethylsilanes. ArCH 2Si(Me)3 derivatives are bench stable reagents yet can serve as benzyl anion equivalents under mild reaction conditions. Following activation with fluoride they can successfully participate in a wide range of additions to both non-enolizable and enolizable carbonyls. In addition, their use in the synthesis of isochromanones and trifluoromethylated amines is illustrated. The broad synthetic scope and mild practical conditions of use for ArCH2Si(Me)3 reagents demonstrate their general potential as benzyl anion equivalents.

Benzylic Grignard Reagents: Application of (thf = tetrahydrofuran) in Regioselective Grignard Formation and C-O Cleavage in Benzyl Ethers

Benzylic Grignard reagents (2)-(4), bearing ortho- and para-halogeno ring substituents, are readily accessible by treating the corresponding benzylic halide with (1) in tetrahydrofuran (thf); o- and p-chloromethyl(methoxymethyl)benzenes with (1) rapidly yield 'di-Grignards' whereas the meta-isomer only affords a mono-Grignard' (5), and bis(methoxymethyl)benzenes slowly undergo C-O cleavage, (6).