178561-30-3

Usage

Uses

Used in Flavoring and Fragrance Industry:
10-Undecene-1-thiol is used as a flavoring agent in food and beverages for its distinctive aromatic properties, enhancing the sensory experience of consumers.
Used in Perfume and Fragrance Production:
10-Undecene-1-thiol is utilized as a component in the creation of perfumes and fragrances, contributing to the development of complex and appealing scents.
Used in Rubber and Plastics Manufacturing:
In the manufacturing of rubber and plastics, 10-Undecene-1-thiol is used as a reactive compound to improve the properties of these materials, such as flexibility and durability.
Used in Pharmaceutical Industry:
10-Undecene-1-thiol is employed in the pharmaceutical industry for its potential applications in drug synthesis and development, leveraging its reactivity and unique chemical characteristics.
Used in Cosmetic Industry:
In cosmetics, 10-Undecene-1-thiol is used for its unique odor and chemical properties, which can be harnessed to create innovative formulations and improve product performance.
Each of these applications takes advantage of 10-Undecene-1-thiol's distinctive features, from its pungent odor to its high reactivity, making it a valuable compound across a range of industries.

Upstream product

• 178561-27-8 S-(undec-10-en-1-yl)ethanthioate 
• 7766-50-9 1-undecen-11-ylbromide 

Downstream Products

• 223646-44-4 ω-undecenyl thiotrifluoroacetate 
• 1292779-37-3 C₈₁H₉₉N₁₃O₁₆S 

Relevant academic research and scientific papers

Surface-initiated polymerization of superhydrophobic polymethylene

We report a new surface-initiated polymerization strategy that yields superhydrophobic polymethylene (PM) films from initially smooth substrates of gold and silicon. The films are prepared by assembling a vinyl-terminated self-assembled monolayer, followed by exposure of the surface to a 0.1 M solution of borane, and polymerizing from the borane sites upon exposure to a solution of diazomethane at -17 °C. Surface-initiated polymethylenation (SIPM) presents rapid growth in relation to other surface-initiated reactions, producing PM films thicker than 500 nm after 2 min of reaction and 3 μm after 24 h of reaction. AFM and SEM images show the presence of micro- and nanoscale features that enable the entrapment of air when exposed to water. Consistent with this result, these films exhibit advancing water contact angles greater than 160°, dramatically different than 103° measured for smooth PM films, and hysteresis values ranging from 2° to 40°, depending on the substrate and polymerization time. The superhydrophobic character of the films results in the entrapment of air at the polymer/solution interface to provide remarkable resistances greater than 1010 ω·cm 2 against the transport of aqueous redox probes and cause the film to behave as a perfect capacitor.

Quantifying Ligand Exchange on InP Using an Atomically Precise Cluster Platform

The surface chemistry of a colloidal nanoparticle is intrinsic to both its structure and function. It is therefore necessary to characterize the surfaces of colloidal materials to rationally underpin any synthetic, catalytic, or transformative mechanisms they enable. Here we characterize the surface properties of colloidal InP clusters and quantum dots by examining the binding of traditional stabilizing ligands including carboxylates, phosphonates, and thiolates. By using the In37P20X51 (X = carboxylate) cluster species as an ideally monodisperse and well-defined starting scaffold, we quantify surface-exchange equilibria. Using quantitative 1H and 31P NMR spectroscopy, we show that 1:1 metathesis-type binding models are insufficient to fully describe the surface dynamics. In particular, for the case of the highly reversible carboxylate ligand exchange, a more detailed isotherm approach using a two-site, competitive model is necessary. This model is used to deconvolute L- A nd X-type binding modalities. We additionally quantify the reversible and irreversible ligand-exchange reactions observed in the thiolate and phosphonate systems.

Detailed structural examinations of covalently immobilized gold nanoparticles onto hydrogen-terminated silicon surfaces

The modification of flat semiconductor surfaces with nanoscale materials has been the subject of considerable interest. This paper provides detailed structural examinations of gold nanoparticles covalently immobilized onto hydrogen-terminated silicon surfaces by a convenient thermal hydrosilylation to form Si-C bonds. Gold nanoparticles stabilized by ω-alkene-1-thiols with different alkyl chain lengths (C3, C6, and C 11), with average diameters of 2-3 nm and a narrow size distribution were used. The thermal hydrosilylation reactions of these nanoparticles with hydrogen-terminated Si(111) surfaces were carried out in toluene at various conditions under N2. The obtained modified surfaces were observed by high-resolution scanning electron microscopy (HR-SEM). The obtained images indicate considerable changes in morphology with reaction time, reaction temperature, as well as the length of the stabilizing ω-alkene-1-thiol molecules. These surfaces are stable and can be stored under ambient conditions for several weeks without measurable decomposition. It was also found that the aggregation of immobilized particles on a silicon surface occurred at high temperature (> 100°C). Precise XPS measurements of modified surfaces were carried out by using a Au-S ligand-exchange technique. The spectrum clearly showed the existence of Si-C bonds. Cross-sectional HR-TEM images also directly indicate that the particles were covalently attached to the silicon surface through Si-C bonds.

Novel method for construction of a metal-organic monolayer-Si structure utilizing thiol-terminated monolayer covalently bonded to the surface through Si-C bonds

An organic monolayer with a thiol group at its end was formed on a hydrogen-terminated (H-) Si(111) surface via Si-C covalent bond by hydrosilylation. PtCl42- complex ions were then immobilized on the thiol-terminated monolayer by immersing the substrate in an aqueous solution of K2PtCl4 using a strong interaction between the Pt complex and thiol groups. The immobilized Pt complexes were then reduced to Pt nanocluster by NaBH4. Precise surface structure was characterized and it is proven that Pt species were indeed deposited only on top of the thiol-terminated monolayer.

High surface density covalent immobilization of oligonucleotide monolayers using a 1-(thiotrifluoroacetato)-11-(trichlorososilyl)-undecane linker

Oligonucleotides and other biomolecules are immobilized in high density on solid substrates through covalent forces using either a permanent thioether bond, or a chemoselectively reversible disulfide bond to a surface thiol. Substrates which have hydroxyl groups on their surfaces can be first silanized with a trichlorosilane containing 2-20 carbon atoms in its hydrocarbon backbone, terminating in a protected thiol group. The oligonucleotides or other biomolecules are first connected to a tether consisting of a hydrocarbon or polyether chain of 2-20 units in length which terminates in a thiol group. This thiol may be further modified with a halobenzylic-bifunctional water soluble reagent which allows the conjugate to be immobilized onto the surface thiol group by a permanent thioether bond. Alternatively, the oligonucleotide-tether-thiol group can be converted to a pyridyldisulfide functionality which attaches to the surface thiol by a chemoselectively reversible disulfide bond. The permanently bound oligonucleotides are immobilized in high density compared to other types of thiol functionalized silane surfaces and to the avidin-biotin method.

Thiol functionalization of surfaces for biosensor development

The immobilization of biomolecules on substrate surfaces for biosensor development requires linking molecules that must meet a specific set of criteria. Two such agents based on bifunctional alkyltrichlorosilane structures, 1-bromo-11-(trichlorosilyl)-undecane and 1-(thiotrifluoroacetato)-11-(trichlorosilyl)-undecane, are employed to generate thiol-functionalized surfaces either by nucleophilic substitution followed by reduction (bromine-containing derivative) or deprotection (fluorine-containing compound). Both molecules have been attached to the surfaces of silicon wafers in conjunction with the diluent silane, octyltrichlorosilane. X-ray photoelectron spectroscopic analysis in the conventional and angle-resolved modes confirms that both silanization reactions were successful. The alkyl-bromine surfaces were subjected to treatment with a set of nucleophilic reactants followed by reduction and derivatization with trifluoroacetic anhydride. The latter in conjunction with surface analysis was used to estimate the level of thiol functionalization achieved. The fluorine-containing undecane surface has been studied by surface analysis both before and after deprotection of the thiol group by hydroxylamine solution. The results indicate that a high coverage of the surface was found for the protected moiety, with approximately 10% of the trifluoro acetate groups remaining after the deprotection procedure.