Triethoxyallylsilane

• CAS: 2550-04-1
• Catalog Number: ACM2550041
• Category: Main Products
• Molecular Weight: 204.34
• Molecular Formula: C9H20O3Si
• Synonyms: triethoxy-2-propenyl-Silane
• Density: 0.903 g/mL
• Appearance: Colorless liquid

Case Study

Triethoxyallylsilane as a Silane Monomer for Antibacterial Hydrophobic Cotton Finishing

Lu, Zhou, et al. Cellulose 26.12 (2019): 7483-7494.

Triethoxyallylsilane (ATEOS) serves as an allyl-functional silane monomer whose hydrosilylation with hydride-terminated polydimethylsiloxane builds a fluorinated pyridinium polysiloxane that imparts durable antibacterial and hydrophobic properties to cotton fabrics.
Experimental Protocol: ATEOS (2.820 g, 13.8 mmol) in toluene is added dropwise over 1 h to a mixture of the siloxane and a platinum catalyst and stirred at 70°C for 12 h under argon; subsequent amination with 4-aminopyridine in tetrahydrofuran at 75°C for 24 h and quaternization with perfluorooctyl iodide at 60°C for 24 h afford the final finishing agent. Reaction progress is followed by the disappearance of the Si-H stretching band near 2126 cm-1 in the infrared spectrum. Cotton fabrics are padded with 2%, 3% or 4% finishing solutions, dried at 90°C for 1 h and cured at 120°C for 5 min.
Performance Evaluation: The intermediate polysiloxane is obtained in 75.46% yield. Treated fabrics show antibacterial rates of 98.99%, 99.49% and 99.49% against Escherichia coli and 99.00%, 99.50% and 99.50% against Staphylococcus aureus, with inhibition zones of 1 mm and 3.5 mm, respectively. Elemental mapping confirms silicon, nitrogen, iodine and fluorine on the treated surface. The water contact angle rises from 71.44° to 122.82°, and thermal stability is improved, confirming multifunctional and durable finishing of the cotton substrate.

Triethoxyallylsilane as an Organosilane Nucleophile for Sulfonylative Hiyama Cross-Coupling

Adenot, Aurélien, et al. Chemical Communications 55.86 (2019): 12924-12927.

Triethoxy(allyl)silane acts as an air-stable silicon nucleophile in a palladium-catalyzed sulfonylative Hiyama cross-coupling that inserts sulfur dioxide between the silane and aryl iodides to deliver allyl aryl sulfones of pharmaceutical relevance.
Experimental Protocol: The allylsilane (1.1 equiv), 4-iodotoluene, sulfur dioxide generated from potassium metabisulfite (2 equiv), tetrabutylammonium difluorophenylsilicate (1 equiv), palladium(II) acetylacetonate (5 mol%) and a xanthene-based diphosphine ligand (10 mol%) are combined in tetrahydrofuran at 80°C for 4 h, and yields are measured by NMR with mesitylene as internal standard. No reaction occurs without the palladium catalyst.
Performance Evaluation: Under optimized conditions the desired allyl sulfone forms in 78% yield, whereas initial screens with a fluoride hydrate source or a sulfur dioxide adduct gave only 12% or no product. A substrate scope of aryl iodides bearing electron-donating or electron-withdrawing groups affords sulfones in 38-82% yield, with a Hammett slope of -0.39 indicating rate-determining reductive elimination; an alkenyl sulfone is obtained in 57% yield. Mechanistic studies reveal a transient allylsulfinate anion that couples with the aryl electrophile, enabling the first sulfonylative process with sp2-hybridized electrophiles. Computational analysis favors an SE2 pathway over ipso substitution for sulfinate formation, with transition-state energies of 25.4 and 29.7 kcal/mol, respectively.

Custom Q&A

What is the molecular formula of Allyltriethoxysilane?

The molecular formula of Allyltriethoxysilane is C9H20O3Si.

What is the molecular weight of Allyltriethoxysilane?

The molecular weight of Allyltriethoxysilane is 204.34 g/mol.

What is the IUPAC name of Allyltriethoxysilane?

The IUPAC name of Allyltriethoxysilane is triethoxy(prop-2-enyl)silane.

What is the InChI of Allyltriethoxysilane?

The InChI of Allyltriethoxysilane is "InChI=1S/C9H20O3Si/c1-5-9-13(10-6-2,11-7-3)12-8-4/h5H,1,6-9H2,2-4H3".

What is the InChIKey of Allyltriethoxysilane?

The InChIKey of Allyltriethoxysilane is "UMFJXASDGBJDEB-UHFFFAOYSA-N".

What is the canonical SMILES of Allyltriethoxysilane?

The canonical SMILES of Allyltriethoxysilane is "CCO[Si](CC=C)(OCC)OCC".

What is the CAS number of Allyltriethoxysilane?

The CAS number of Allyltriethoxysilane is 2550-04-1.

What is the EC number of Allyltriethoxysilane?

The EC number of Allyltriethoxysilane is 219-843-2.

What is the hydrogen bond donor count of Allyltriethoxysilane?

The hydrogen bond donor count of Allyltriethoxysilane is 0.

Is Allyltriethoxysilane a canonicalized compound?

Yes, Allyltriethoxysilane is a canonicalized compound.