18670-61-6

Usage

Uses

Used in Organic Synthesis:
(bromomethyl)(triphenyl)silane is used as a reagent for the introduction of the bromomethyl group into organic molecules, facilitating the synthesis of a wide range of organic compounds.
Used in Materials Science:
In the field of materials science, (bromomethyl)(triphenyl)silane is studied for its potential applications, including the development of new materials with unique properties.
Used as a Precursor in Organosilicon Polymers Synthesis:
(bromomethyl)(triphenyl)silane serves as a precursor in the synthesis of organosilicon polymers, which have a variety of applications in industries such as electronics, coatings, and adhesives.
Used in Chemical Reactions with Nucleophiles:
Due to its high reactivity, (bromomethyl)(triphenyl)silane is utilized in various chemical reactions with nucleophiles, allowing for the formation of new compounds and contributing to the advancement of organic chemistry.

Upstream product

• 75-25-2 Bromoform 
• 76-86-8 Triphenylsilyl chloride 
• 791-30-0 triphenylsilyl-lithium 
• 789-25-3 HSiPh₃ 
• 15409-72-0 (dibromomethyl)triphenylsilane 
• 18670-80-9 triphenylsilanyl-methanol 

Downstream Products

• 18666-58-5 triphenylsilylacetic acid 
• 791-29-7 methyltriphenylsilane 
• 18822-04-3 1,2-bis(triphenylsilyl)ethane 
• 18790-80-2 1-phenyl-2-(triphenylsilyl)ethanol 
• 862970-58-9 1,3-diphenyl-1-[(triphenylsilanyl)-methyl]-urea 
• 15812-05-2 1-Triphenylsilyl-2-phenyl-aethanon-⁽²⁾ 
• 862970-54-5 phenyl-[(triphenylsilanyl)-methyl]-amine 

Relevant academic research and scientific papers

Electronic effects and the stereochemistries in rearrangement-displacement reactions of triaryl(halomethyl)silanes with fluoride and with alkoxide ions

Tetrabutylammonium fluoride (TBAF) reacts with (halomethyl)diphenyl(para-substituted-phenyl)silanes (13, X = Cl), 14 (X = Br), and 15 (X = I) in ether solvents to give fluorodiphenyl(parasubstituted-phenylmethyl)silanes (17a) and fluorophenyl(phenylmethyl)(para-substituted-phenyl)silanes (20a) by attack on silicon and migrations of the phenyl or the para-substituted-phenyl groups to C-1 with displacement of chloride ion. Sodium methoxide in dioxane effects rearrangement displacements of 14 (X = Br) to yield methoxydiphenyl(para-substituted-phenylmethyl)silanes (17b) and methoxyphenyl(phenylmethyl)(para-substituted-phenyl)silanes (20b). The migratory aptitudes of the varied phenyl groups in rearrangement-displacements of 13 with F- at 25°C are p-CF3-Ph, 2.72 > p-Cl-Ph, 1.67 > Ph, 1.00 > p-CH3-Ph, 0.91 > p-CH3O-Ph, 0.58 > p-(CH3)2N-Ph, 0.55. For reactions of 14 with sodium methoxide in dioxane, the migratory aptitudes at 23°C are p-CF3-Ph, 2.53 > p-Cl-Ph, 1.64 > Ph, 1.00 > p-CH3O-Ph, 0.84 > p-CH5-Ph, 0.79 > p-(CH3)2N-Ph, 0.68. The migratory aptitudes in the above rearrangement-displacements are increased by electron withdrawing substituents, and logarithms of the migratory aptitudes give satisfactory linear correlations with σ and/or σ-zero values of the phenyl substituents. Hammett correlations however of the migratory aptitudes from reactions of F- with 13 (X = Cl) at 0 and -20°C, 14 (X = Br) at 23, 0, and -20°C, and 15 (X = I) at 23°C are not linear. (+)-(Bromomethyl)methyl-1 naphthylphenylsilane (23, [α]D23 +8.29°, cyclohexane) reacts with CsF and with TBAF in THF to give benzylfluoromethyl-1-naphthylsilane (51, [α]D25 = 0.00°, cyclohexane) and fluoromethyl-(1 naphthylmethyl)phenylsilane (52, impure) in 10.4:1 ratio along with unchanged 23 ([α]D23 8.29°, cyclohexane). Sodium methoxide and (+)-23 in dioxane at 25°C and at 0°C yield (+)benzylmethoxymethyl-1-naphthylsilane (64) and (+)-methoxymethyl(1-naphthylmethyl)phenylsilane (65) in ～9:1 ratio. The conversions of (+)-23 to (+)-64 occur with 93% inversion about silicon. Reaction of (+)-23 with sodium methoxide at 25°C to give (+)-65 also occurs with inversion. Further, sodium ethoxide and sodium 2-propoxide react with (+)-23 at 20-25°C by rearrangement displacements on silicon with phenyl migrations to yield (+)-benzylethoxymethyl-1-naphthylsilane (69) and (+)-benzylmethyl-1-naphthyl-2-propoxysilane (70), respectively, each with 95% inversion about silicon. The mechanisms of rearrangement-displacements of 13-15 and (+)-23 by fluoride and by alkoxide ions are discussed.

Bromo-di(silyl)methanes - Precursors to Disilylcarbanionic Ligands

The reaction of the series of methyl/phenylchlorosilanes Me2PhSiCl, MePh2SiCl and Ph3SiCl with CHBr3/n-BuLi to give the corresponding bromo-di(silyl)methanes has been investigated.The selectivity of the reaction proved to be strongly influenced by the num