Tetraoctyltin

• CAS: 3590-84-9
• Catalog Number: ACM3590849
• Category: Main Products
• Molecular Weight: 571.59
• Molecular Formula: C32H68Sn
• Synonyms: tetra-n-octylstannane
• Appearance: Celar liquid

Case Study

Tetraoctyltin: A Lewis Acid Catalyst for Bioactive Hybrid Material Synthesis

Sokolik, Chana G., et al. RSC advances 8.64 (2018): 36712-36721.

The development of advanced delivery systems for natural biocides, such as carvacrol from oregano and thyme, requires precise chemical synthesis to overcome inherent limitations like poor solubility and stability. A key step involves covalently linking the bioactive molecule to a silica-based carrier through a hydrolyzable bond, enabling controlled release. This study highlights the role of Tetraoctyltin as a specialized catalyst critical to constructing this linkage efficiently.
In the synthesis of a hybrid silica nanoparticle system, Tetraoctyltin was employed as a Lewis acid catalyst. Its function was to promote the carbamoylation reaction between carvacrol and 3-(triethoxysilyl)propyl isocyanate, forming the enzymatically cleavable carbamate bond that anchors the biocide to the eventual silica matrix. This catalytic step is essential for creating the "release-on-demand" precursor molecule.
Catalytic Mechanism and Performance: Tetraoctyltin acts by forming a catalytically active complex with the electron-donating alcohol (carvacrol) and isocyanate reactants. A significant feature of this catalyst is its bulky octyl substituents. These groups are reported to depress the complexation of the reaction product (the carbamate) with the tin center, thereby preventing catalyst deactivation and maintaining a higher concentration of active catalyst throughout the reaction. The reaction, conducted at room temperature under a nitrogen atmosphere for over 15 hours using Tetraoctyltin, yielded the target carbamate-linked silane precursor with a reported yield ranging from 35% to 54%.

Tetraoctyltin: Enabling Enhanced Antimicrobial Nanomaterials through Catalytic Synthesis

Makarovsky, Igor, et al. Advanced Functional Materials 21.22 (2011): 4295-4304.

Developing advanced antimicrobial materials that offer controlled, sustained release is crucial in combating bacterial resistance. The synthesis of the crucial molecular linker that tethers the biocide to the delivery system requires a highly effective catalyst. In the development of triclosan-bound hybrid-silica nanoparticles (T-SNPs), Tetraoctyltin was employed to catalyze the key carbamoylation reaction. Its role was to facilitate the formation of a hydrolysable carbamate bond between triclosan, an FDA-approved antimicrobial, and 3-isocyanatopropyltriethoxysilane. This reaction produced the novel silane precursor essential for constructing the nanoparticle matrix with covalently integrated, releasable biocide.
Key Performance:
· Efficient Catalysis for Scalable Synthesis: The Tetraoctyltin-catalyzed reaction proceeded at room temperature and provided a 64% yield of the target carbamate-linked silane (TTESPC). This efficient and relatively facile process is noted for its potential for easy scale-up.
· The nanoparticles synthesized from this precursor were spherical, with a diameter of 130 ± 30 nm. Biological testing revealed that these T-SNPs exhibited a 5-6 log increase in bacterial killing capacity compared to free triclosan, demonstrating the success of the controlled-release design enabled by the initial catalytic step.

Custom Q&A

What is the molecular formula of Tetraoctyltin?

The molecular formula of Tetraoctyltin is C32H68Sn.

What is the molecular weight of Tetraoctyltin?

The molecular weight of Tetraoctyltin is 571.6 g/mol.

When was Tetraoctyltin created?

Tetraoctyltin was created in 2005-03-26.

What are some synonyms for Tetraoctyltin?

Some synonyms for Tetraoctyltin include Tetraoctylstannane and Tetra-n-octyltin.

What is the IUPAC name of Tetraoctyltin?

The IUPAC name of Tetraoctyltin is tetraoctylstannane.

What is the InChIKey of Tetraoctyltin?

The InChIKey of Tetraoctyltin is JTGNPNLBCGBCMP-UHFFFAOYSA-N.

How many hydrogen bond donor counts does Tetraoctyltin have?

Tetraoctyltin has 0 hydrogen bond donor counts.

What is the exact mass of Tetraoctyltin?

The exact mass of Tetraoctyltin is 572.434305 g/mol.

How many rotatable bond counts does Tetraoctyltin have?

Tetraoctyltin has 28 rotatable bond counts.

How many defined atom stereocenter counts does Tetraoctyltin have?

Tetraoctyltin has 0 defined atom stereocenter counts.