(BROMOETHYNYL)TRIISOPROPYLSILANE Manufacturer CAS No.:111409-79-1

What is (Bromoethynyl)Triisopropylsilane?

(Bromoethynyl)Triisopropylsilane CAS No.:111409-79-1 is an organosilicon compound known for its utility in organic synthesis. The compound features a bromoethynyl group attached to a triisopropylsilane moiety, combining the reactivity of the brominated alkyne with the steric protection provided by the bulky triisopropylsilane group.

Properties

1. Alkyne Reactivity:
   • The bromoethynyl group is highly reactive, especially in nucleophilic substitution and metal-catalyzed coupling reactions.
2. Steric Protection:
   • The triisopropylsilane group is bulky, providing steric protection to the alkyne, which can be useful in selective synthetic applications.
   • This bulky group can also help in stabilizing the alkyne against premature polymerization or side reactions.
3. Stability:
   • The compound is relatively stable under standard conditions but reactive under specific synthetic protocols.
4. Solubility:
   • Soluble in organic solvents, making it easy to handle and use in various organic reactions.

Main Applications

(Bromoethynyl)Triisopropylsilane is predominantly used in organic synthesis, where it serves as a versatile building block for introducing bromoalkyne groups into complex molecules. Its applications include:

1. Cross-Coupling Reactions:
   • Sonogashira Coupling: The bromoethynyl group can participate in Sonogashira cross-coupling reactions with aryl or vinyl halides, forming substituted alkynes. This reaction is pivotal in the synthesis of complex organic molecules, including natural products and pharmaceuticals.
   • Other Metal-Catalyzed Couplings: The bromoethynyl moiety can engage in various metal-catalyzed coupling reactions, facilitating the formation of carbon-carbon or carbon-heteroatom bonds.
2. Synthesis of Conjugated Systems:
   • Organic Electronics: We use it to synthesize conjugated systems for organic electronics, including organic semiconductors and conductive polymers.
   • Polymers and Dendrimers: It is a precursor for synthesizing polymers and dendrimers with alkyne functionalities, we further modify it through click chemistry or other reactions.
3. Functional Group Transformation:
   • We can remove the triisopropylsilane group under mild conditions, revealing the alkyne for further functionalization.
   • This deprotection step is useful in multistep synthesis where protecting groups are needed to control the reactivity of functional groups.
4. Introduction of Bromoalkyne Moieties:
   • The bromoethynyl group is a versatile synthon for introducing bromoalkyne functionalities into organic molecules, which can be further elaborated through various chemical transformations.

Advantages in Synthetic Chemistry

1. High Reactivity:
   • The bromoethynyl group is highly reactive, enabling efficient coupling and substitution reactions.
   • This reactivity is particularly useful in forming new carbon-carbon bonds.
2. Steric Control:
   • The bulky triisopropylsilane group provides steric protection, allowing for selective reactions and preventing side reactions or polymerization of the alkyne.
3. Versatility:
   • We use the compound in a wide range of synthetic applications, from cross-coupling reactions to the synthesis of complex molecular architectures.
4. Ease of Handling:
   • Its stability and solubility in organic solvents make it easy to handle and use in laboratory settings.

Examples of Applications in Synthesis

1. Pharmaceuticals:
   • We use it in the synthesis of drug candidates and desire the alkyne functionality for further modifications or bioactive properties.
2. Natural Products:
   • Employed in the construction of complex natural products with alkyne groups, which are often found in biologically active molecules.
3. Material Science:
   • Used in the development of advanced materials, such as organic light-emitting diodes (OLEDs) and other optoelectronic devices, where conjugated systems are crucial.
4. Bioconjugation:
   • We can attach this compound to attach alkyne groups to biomolecules, facilitating their modification or conjugation through click chemistry.

Conclusion

(Bromoethynyl)Triisopropylsilane is a valuable reagent in organic synthesis, particularly in reactions involving the introduction and transformation of alkyne functionalities. Its unique combination of a reactive bromoethynyl group and a protective triisopropylsilane moiety makes it a versatile tool in constructing complex organic molecules. Its applications span across pharmaceuticals, materials science, and advanced organic synthesis, making it an indispensable compound in modern synthetic chemistry.