Triphenylsilanol
[CAS# 791-31-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Silane
• Name: Triphenylsilanol
• Synonyms: Hydroxytriphenylsilane
• Molecular Formula: C₁₈H₁₆OSi
• Molecular Weight: 276.41
• CAS Registry Number: 791-31-1
• EC Number: 212-339-3
• SMILES: C1=CC=C(C=C1)[Si](C2=CC=CC=C2)(C3=CC=CC=C3)O

Properties

• Water solubility: reacts
• Density: 1.1±0.1 g/cm³, Calc.^*, 1.17 g/mL
• Melting point: 150-153 ºC
• Index of Refraction: 1.629, Calc.^*
• Boiling Point: 388.6±15.0 ºC (760 mmHg), Calc.^*
• Flash Point: 188.8±20.4 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

Triphenylsilanol, also known as triphenylsiloxy, is an organosilicon compound that has garnered attention for its unique chemical properties and diverse applications. Comprising a silicon atom bonded to three phenyl groups and one hydroxyl group, triphenylsilanol is classified as a silanol, which are compounds containing a hydroxyl group attached to a silicon atom. The discovery of triphenylsilanol dates back to the early 20th century when researchers were investigating the properties of organosilicon compounds and their potential uses in various fields.

The initial synthesis of triphenylsilanol was achieved through the hydrolysis of triphenylsilane, a process that involves the reaction of water with the silicon atom in triphenylsilane, replacing one of the phenyl groups with a hydroxyl group. This transformation was significant in expanding the understanding of silanol chemistry and paved the way for the development of other silanol derivatives. The distinctive structure of triphenylsilanol, featuring both siloxane and phenyl functionalities, contributes to its versatility in various applications.

One of the primary applications of triphenylsilanol is in the field of materials science. It serves as a valuable precursor for synthesizing various silicone-based materials, including elastomers and resins. Due to its ability to form cross-linked networks, triphenylsilanol is incorporated into formulations to enhance the mechanical properties and thermal stability of silicone products. This application is particularly important in industries such as automotive, electronics, and construction, where durable and heat-resistant materials are essential.

In addition to its role in material science, triphenylsilanol has found applications in organic synthesis. Its unique chemical properties allow it to act as a reagent in various chemical transformations. For example, triphenylsilanol can be employed as a protecting group for hydroxyl functionalities in organic molecules, facilitating selective reactions. This capability is especially useful in multi-step synthetic processes, where the protection and deprotection of functional groups are critical for achieving desired products.

Moreover, triphenylsilanol exhibits potential applications in the pharmaceutical industry. Its silanol group has been shown to interact with biological systems, making it a candidate for drug formulation and delivery. Research is ongoing to explore its effectiveness as a solubilizing agent for poorly water-soluble drugs, as well as its ability to enhance the bioavailability of active pharmaceutical ingredients. By improving the solubility and stability of drugs, triphenylsilanol could contribute to more effective therapeutic options.

Environmental applications of triphenylsilanol have also been investigated. Its unique properties allow it to act as a surfactant in various formulations, enabling improved dispersibility and stability of emulsions. This function is particularly beneficial in agrochemicals, where triphenylsilanol can enhance the efficacy of pesticide formulations by ensuring even distribution and adherence to plant surfaces.

Despite its numerous advantages, the use of triphenylsilanol requires careful consideration of safety and environmental impacts. Regulatory assessments are necessary to ensure that products containing this compound meet safety standards, particularly in consumer applications such as cosmetics and personal care products. Ongoing research is focused on evaluating its toxicity and environmental behavior to ensure safe use.

In conclusion, triphenylsilanol is a versatile organosilicon compound with significant applications in materials science, organic synthesis, pharmaceuticals, and environmental science. Its unique chemical structure enables it to serve as a precursor for various silicone-based materials and a valuable reagent in organic chemistry. As research continues to unveil its potential in new applications, triphenylsilanol remains an important compound in modern chemistry and industry.