214268-06-1

Basic information

• Product Name: 3-TRIMETHYLSILYLPROPARGYLMETHACRYLATE, 95%
• Synonyms: 3-TRIMETHYLSILYLPROPARGYLMETHACRYLATE, 95%
• CAS NO: 214268-06-1
• Molecular Formula: C₁₀H₁₆O₂Si
• Molecular Weight: 195.3104
• Mol File: 214268-06-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C
• CAS DataBase Reference: 3-TRIMETHYLSILYLPROPARGYLMETHACRYLATE, 95%(CAS DataBase Reference)
• NIST Chemistry Reference: 3-TRIMETHYLSILYLPROPARGYLMETHACRYLATE, 95%(214268-06-1)
• EPA Substance Registry System: 3-TRIMETHYLSILYLPROPARGYLMETHACRYLATE, 95%(214268-06-1)

Safety Data

• Hazardous Substances Data: 214268-06-1(Hazardous Substances Data)

Upstream product

• 920-46-7 Methacryloyl chloride 
• 5272-36-6 3-trimethylsilyl-2-propyn-1-ol 
• 75-77-4 chloro-trimethyl-silane 
• 13861-22-8 prop-2-yn-1-yl methacrylate 

Downstream Products

• 13861-22-8 prop-2-yn-1-yl methacrylate 

Relevant articles and documents

Efficient fabrication of polymer nanoparticles via sonogashira cross-linking of linear polymers in dilute solution

The synthesis of single-chain nanoparticles by palladium-catalyzed Sonogashira coupling between a terminal alkyne and a di-halo aryl cross-linker is reported. Statistical copolymers with trimethylsilyl protected alkyne groups pendent to the linear methacr

Synthesis of multifunctional polymer brush surfaces via sequential and orthogonal thiol-click reactions

Fabrication of multifunctional surfaces with complexity approaching that found in nature requires the application of a modular approach to surface engineering. We describe a versatile post-polymerization modification strategy to synthesize multifunctional polymer brush surfaces via combination of surface-initiated photopolymerization (SIP) and orthogonal thiol-click reactions. Specifically, we demonstrate two routes to multifunctional brush surfaces: in the first approach, alkyne-functionalized homopolymer brushes are modified with multiple thiols via a statistical, radical-mediated thiol-yne co-click reaction; and in the second approach, statistical copolymer brushes carrying two distinctly-addressable reactive moieties are sequentially modified via orthogonal base-catalyzed thiol-X (where X represents an isocyanate, epoxy, or α-bromoester) and radical-mediated thiol-yne reactions. In both cases, we show that surface properties, in the form of wettability, can be easily tuned over a wide range by judicious choice of brush composition and thiol functionality. The Royal Society of Chemistry 2011.

Formation of giant amphiphiles by post-functionalization of hydrophilic protein-polymer conjugates

A novel, generic method for the synthesis of families of tri-block protein-polymer giant amphiphiles was designed and developed. We have synthesized a hydrophilic α-maleimido poly-1-alkyne with Mn = 9.5 kDa (1H-NMR) and narrow PDi (1.15 as measured by SEC) via ATRP (Atom Transfer Radical Polymerization). This polymer was succesfully coupled to BSA to afford a hydrophilic multifunctional bioconjugate which was isolated using protein purification techniques and fully characterized. Following the post-functionalization approach, we introduced hydrophobicity to the resulting hydrophilic biohybrid by a straightforward, high yield "click"- chemistry cycloaddition step. The resulting tri-block protein-polymer amphiphiles were isolated and showed interesting aggregation patterns (TEM, confocal microscopy). The Royal Society of Chemistry 2007.

Comb-shaped graft copolymers with cellulose side-chains prepared via click chemistry

Comb-shaped copolymers with cellobiose acetate or cellulose triacetate (CTA) side-chains, PPMA-g-(CTA2-C15) and PPMA-g-(CTA13-C15), were prepared by grafting N-(15-azidopentadecanoyl)-2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O- acetyl-β-d-glucopyranosyl)-β-d-glucopyranosylamine (CTA2-C15-N 3) and N-(15-azidopentadecanoyl)-tri-O-acetyl-β-cellulosylamine (CTA13-C15-N3, number average degree of polymerization (DP n) = 13) onto poly(2-propyn-1-yl methacrylate) (PPMA, weight average degree of polymerization (DPw, X + Y = 5.59 × 102)) via "click chemistry". The copolymers were characterized by 1H, 13C and two-dimensional NMR and size exclusion chromatography-multi-angle laser light scattering (SEC-MALS) measurements. The numbers of CTA side-chains (X) of PPMA-g-(CTA2-C15) and PPMA-g-(CTA13-C15) were calculated as 4.03 × 102 and 2.45 × 102, respectively. Copolymers with cellulosic side-chains, PPMA-g-(CELL2-C15) and PPMA-g-(CELL13-C15), were successfully obtained after deacetylation of PPMA-g-(CTA2-C15) and PPMA-g-(CTA13-C15), respectively. X-ray diffraction measurements revealed that PPMA-g-(CELL13-C15) showed crystalline pattern of cellulose II, which is believed to have anti-parallel orientation.

Fluorescent and Water Dispersible Single-Chain Nanoparticles: Core–Shell Structured Compartmentation

Single-chain nanoparticles (SCNPs) are highly versatile structures resembling proteins, able to function as catalysts or biomedical delivery systems. Based on their synthesis by single-chain collapse into nanoparticular systems, their internal structure is complex, resulting in nanosized domains preformed during the crosslinking process. In this study we present proof of such nanocompartments within SCNPs via a combination of electron paramagnetic resonance (EPR) and fluorescence spectroscopy. A novel strategy to encapsulate labels within these water dispersible SCNPs with hydrodynamic radii of ≈5 nm is presented, based on amphiphilic polymers with additional covalently bound labels, attached via the copper catalyzed azide/alkyne “click” reaction (CuAAC). A detailed profile of the interior of the SCNPs and the labels’ microenvironment was obtained via electron paramagnetic resonance (EPR) experiments, followed by an assessment of their photophysical properties.

Application of polymer microspheres to Raman detection

The invention discloses application of polymer microspheres to Raman detection. Methacrylate/amide polymer monomers or styrene polymer monomers containing alkynyl, cyano, azido or a carbon-deuterium bond group are prepared into the polymer microspheres with the particle diameter from a nanometer grade to a micron grade through an emulsion polymerization or dispersion polymerization method; the polymer microspheres have a remarkable Raman signal under the condition of no metal sensitization structure; and a Raman characteristic peak signal is located in a Raman quiet zone (1800cm to 2800cm) in a living organism and can be used as a marker for biological imaging.

Glycosylated Reversible Addition-Fragmentation Chain Transfer Polymers with Varying Polyethylene Glycol Linkers Produce Different Short Interfering RNA Uptake, Gene Silencing, and Toxicity Profiles

Achieving efficient and targeted delivery of short interfering (siRNA) is an important research challenge to overcome to render highly promising siRNA therapies clinically successful. Challenges exist in designing synthetic carriers for these RNAi constructs that provide protection against serum degradation, extended blood retention times, effective cellular uptake through a variety of uptake mechanisms, endosomal escape, and efficient cargo release. These challenges have resulted in a significant body of research and led to many important findings about the chemical composition and structural layout of the delivery vector for optimal gene silencing. The challenge of targeted delivery vectors remains, and strategies to take advantage of nature's self-selective cellular uptake mechanisms for specific organ cells, such as the liver, have enabled researchers to step closer to achieving this goal. In this work, we report the design, synthesis, and biological evaluation of a novel polymeric delivery vector incorporating galactose moieties to target hepatic cells through clathrin-mediated endocytosis at asialoglycoprotein receptors. An investigation into the density of carbohydrate functionality and its distance from the polymer backbone is conducted using reversible addition-fragmentation chain transfer polymerization and postpolymerization modification.

Controlling the lectin recognition of glycopolymers: Via distance arrangement of sugar blocks

The arrangement of sugars in glycopolymers contributes to their recognition. The molecular recognition of proteins was controlled by the living radical polymerization of glycopolymers. The glycopolymers were prepared by the copolymerization of propargyl methacrylate (Pr-MA) and triethyleneglycol methacrylate (TEG-MA) via living radical polymerization with a reversible addition-fragmentation glycopolymer chain transfer (RAFT) reagent and by subsequent sugar conjugation by click chemistry. The block copolymers were prepared by the polymerization of Pr-MA and TEG-MA. The molecular recognition of glycopolymers was analyzed using the fluorescence quenching of lectin and found to be dependent on the glycopolymer structures. Two-site binding of glycopolymers to concanavalin A (ConA) was attained by both the glycopolymer with a 105-mer and the tri-block glycopolymer with a 103-mer. Glycopolymers with either a 27- or 54-mer showed much weaker interaction because of one-site binding. The molecular recognition of the glycopolymer was controlled by the arrangement and size of the sugar cluster and not by the sugar density.

NEW CLICKABLE POLYMERS AND GELS FOR MICROARRAY AND OTHER APPLICATIONS

Fabrication of arrays, including glycan arrays, that combines the higher sensitivity of a layered Si-SiO2 substrate with novel immobilization chemistry via a "click" reaction. The novel immobilization approach allows the oriented attachment of glycans on a "clickable" polymeric coating. The surface equilibrium dissociation constant (KD) of Concanavalin A with eight synthetic glycans was determined using fluorescence microarray. The sensitivity provided by the novel microarray substrate enables the evaluation of the influence of the glycan surface density on surface KD values. The interaction of carbohydrates with a variety of biological targets, including antibodies, proteins, viruses and cells are of utmost importance in many aspects of biology. Glycan microarrays are increasingly used to determine the binding specificity of glycan-binding proteins. The click polymers can be prepared in different forms such as soluble polymers, hydrogels, and multi-layers. The polymers can be prepared directly by copolymerization or by copolymerization to form a pre-polymer which is then reacted to form the target polymer. Other uses include separations, including electrophoretic separations.

The dual-role of Pt(iv) complexes as active drug and crosslinker for micelles based on β-cyclodextrin grafted polymer

With a combination of RAFT and click chemistry an amphiphilic block copolymer with poly(ethylene glycol) methyl ether methacrylate (POEGMEMA) as hydrophilic block and poly(propargyl methacrylate) (PMA) as hydrophobic block has been successfully synthesized. To this, 6-azide-6-deoxy-β-cyclodextrin (N3-β-CD) was clicked creating a hosting environment for a hydrophobic small molecule platinum pro-drug. Oxoplatin, the oxidized version of cisplatin, has been modified on its axial ligand introducing cholic acid groups through esterification. This modified cisplatin forms a host-guest complex with β-cyclodextrin that has been characterised via NMR spectroscopy. The host-guest interaction that the drug established with the β-cyclodextrin grafted copolymer drove the self-assembly into nanoparticles of a diameter of 266 nm able to physical encapsulate the platinum-based drug. In the presence of ascorbic acid, 70% of the pro-drug is released over a period of 24 h. Cytotoxicity assays on ovarian cancer cells show that the polymer carrier improves the cytotoxicity of the platinum pro-drug. The IC50 value decreases from 37.7 μM with the pro-drug to 20.4 μM when the pro-drug is encapsulated into the polymer carrier. This is due to the fact that the uptake of the polymer carrier is up to 6 fold higher than the significantly smaller pro-drug by itself.