Stannocene
[CAS# 1294-75-3]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organotin
• Name: Stannocene
• Synonyms: Cyclopentane ?2-stannane
• Molecular Formula: C₁₀H₁₀Sn
• Molecular Weight: 248.90
• CAS Registry Number: 1294-75-3
• SMILES: C1CCCC1.C1CCCC1.[SnH2]

Properties

• Melting point: 105 ºC

Discovory and Applicatios

Stannocene, also known as bis(cyclopentadienyl)tin or tin(IV) cyclopentadienyl complex, is a synthetic organotin compound that has garnered attention in the fields of organic chemistry and materials science. The discovery of stannocene dates back to the early 1970s when researchers were exploring the coordination chemistry of tin. It was identified as a stable organometallic complex featuring a tin atom coordinated to two cyclopentadienyl anions. This unique structure not only highlights the versatility of tin as a central metal in organometallic chemistry but also opened avenues for the development of new materials and catalysts.

The significance of stannocene lies in its diverse applications across various fields. One of its primary uses is in the synthesis of organic compounds, where it acts as a reagent in reactions such as nucleophilic substitutions and coupling reactions. Stannocene has been particularly valuable in the preparation of complex organic molecules, enabling the development of pharmaceuticals, agrochemicals, and fine chemicals. Its ability to participate in cross-coupling reactions has made it an essential tool for synthetic chemists seeking to construct carbon-carbon bonds efficiently.

In addition to its synthetic utility, stannocene has gained interest for its potential applications in materials science. The compound exhibits interesting electronic properties, which can be exploited in the development of novel materials. For instance, stannocene has been studied for use in organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs), where its electronic characteristics can enhance device performance. Its incorporation into polymer matrices has also been explored, leading to materials with improved thermal stability and mechanical properties.

Stannocene is typically synthesized through the reaction of tin(IV) chloride with cyclopentadiene in the presence of a reducing agent. This method allows for the efficient formation of the stannocene complex, which can then be purified for further use. The resulting compound is a yellowish solid that can be handled and stored under inert conditions to prevent decomposition or reaction with moisture.

Despite its promising applications, the use of stannocene and other organotin compounds has raised environmental and health concerns. Organotin compounds have been scrutinized for their potential toxicity and bioaccumulation in aquatic ecosystems. Regulatory bodies have established guidelines for the use of organotin compounds, emphasizing the need for careful management and evaluation of their environmental impact.

In summary, stannocene is a significant organotin compound that emerged from the exploration of tin coordination chemistry in the early 1970s. Its applications in organic synthesis, materials science, and electronics highlight its versatility as a reagent and material enhancer. While its potential has been widely recognized, ongoing research and regulatory scrutiny are essential to address the environmental and health implications associated with its use. As the demand for efficient synthetic methodologies and advanced materials continues to grow, stannocene remains a compound of interest in both academic and industrial settings.