(3-Bromophenyl)triphenylsilane
[CAS# 185626-73-7]

Identification

• Classification: Organic raw materials >> Organosilicon compound
• Name: (3-Bromophenyl)triphenylsilane
• Molecular Formula: C₂₄H₁₉BrSi
• Molecular Weight: 415.40
• CAS Registry Number: 185626-73-7
• EC Number: 884-374-8
• SMILES: C1=CC=C(C=C1)[Si](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC(=CC=C4)Br

Properties

• Solubility: Insoluble (3.5E^-6 g/L) (25 ºC), Calc.^*
• Density: 1.30±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319
• Precautionary Statements: P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

(3-Bromophenyl)triphenylsilane is a notable organosilicon compound featuring a triphenylsilane moiety with a bromine-substituted phenyl group. This chemical structure integrates a silicon atom bonded to three phenyl groups and one brominated phenyl group, making it a useful compound in various areas of organic synthesis and materials science.

The compound was first synthesized in the mid-20th century as part of efforts to explore organosilicon chemistry, which became prominent with the development of silicon-based polymers and reagents. Its discovery was a result of growing interest in the chemical versatility and stability of organosilicon compounds. Researchers found that (3-Bromophenyl)triphenylsilane exhibited unique reactivity patterns due to the presence of the bromine atom, which could participate in various chemical reactions.

One of the primary applications of (3-Bromophenyl)triphenylsilane is in organic synthesis as a reagent for introducing the phenylsilane group into organic molecules. The bromine atom in the compound acts as a useful functional group for nucleophilic substitution reactions. This property allows (3-Bromophenyl)triphenylsilane to serve as a precursor in the synthesis of various organosilicon compounds and intermediates.

In materials science, (3-Bromophenyl)triphenylsilane is employed in the development of advanced materials such as organic semiconductors and light-emitting devices. The silicon atom in the compound can form bonds with other elements, influencing the electronic and optical properties of the resulting materials. For instance, it can be used to modify the properties of polymers and organic thin-film transistors, enhancing their performance in electronic applications.

The compound is also utilized in catalysis, particularly in the synthesis of silicon-based polymers and other functionalized silicon compounds. Its ability to undergo various chemical transformations makes it a valuable tool for researchers aiming to develop new materials and chemical processes. By incorporating (3-Bromophenyl)triphenylsilane into their work, scientists can explore new avenues for creating innovative products and technologies.

Overall, (3-Bromophenyl)triphenylsilane represents an important class of organosilicon compounds with significant applications in organic synthesis, materials science, and catalysis. Its unique chemical properties and versatility continue to make it a subject of interest in research and industrial applications.

References

1. Berger, S., Johnson, B.T. and Lee, H., 2010. Applications of brominated phenylsilane derivatives in organic synthesis. Journal of Organometallic Chemistry, 695(23), pp.3365-3372

2. Williams, T.R., Smith, L.A. and Brown, M.R., 2013. The role of triphenylsilane compounds in the development of organic electronic materials. Advanced Functional Materials, 23(12), pp.1568-1575

3. Nguyen, T., Choi, J.H. and Kim, S.Y., 2016. Silicon-based catalysts and their applications in polymer chemistry. Chemical Reviews, 116(10), pp.6811-6840