134874-49-0

Basic information

• Product Name: MERCAPTO POLYETHYLENE GLYCOL 5,000 MONOMETHYL ETHER
• Synonyms: PEG-THIOL;O-(2-MERCAPTOETHYL)-O'-METHYLPOLYETHYLENE GLYCOL 5,000;MERCAPTO POLYETHYLENE GLYCOL 5,000 MONOMETHYL ETHER;MPEGn-SH 2K, 5K, 10K, 20K;O-(2-Mercaptoethyl)-O′-methylpolyethylene glycol;Polyethylene glycol 2-mercaptoethyl methyl ether;O-(2-Mercaptoethyl)-O'-methylpolyethylene glycol 2,000;Poly(ethylene glycol) methyl ether thiol (Mn 2000)
• CAS NO: 134874-49-0
• Molecular Formula: C25H52O12S
• Molecular Weight: 576.73818
• Product Categories: Polydispersed PEG
• Mol File: 134874-49-0.mol
• Article Data: 18

Chemical Properties

• Appearance: /
• CAS DataBase Reference: MERCAPTO POLYETHYLENE GLYCOL 5,000 MONOMETHYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: MERCAPTO POLYETHYLENE GLYCOL 5,000 MONOMETHYL ETHER(134874-49-0)
• EPA Substance Registry System: MERCAPTO POLYETHYLENE GLYCOL 5,000 MONOMETHYL ETHER(134874-49-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 134874-49-0(Hazardous Substances Data)

Usage

Description

MERCAPTO POLYETHYLENE GLYCOL 5,000 MONOMETHYL ETHER, also known as m-PEG12-thiol, is a PEG linker that contains a thiol group. This thiol group is capable of reacting with various compounds such as maleimide, OPSS, vinylsulfone, and transition metal surfaces, including gold and silver. The hydrophilic PEG spacer in m-PEG12-thiol enhances its solubility in aqueous media, making it a versatile molecule for various applications.

Uses

Used in Bioconjugation:
MERCAPTO POLYETHYLENE GLYCOL 5,000 MONOMETHYL ETHER is used as a bioconjugation agent for the formation of stable covalent bonds with maleimide, OPSS, vinylsulfone, and transition metal surfaces. The thiol group in m-PEG12-thiol allows for the attachment of biomolecules, such as proteins or peptides, to various surfaces or other molecules, facilitating the development of novel bioconjugates and biomaterials.
Used in Drug Delivery Systems:
In the pharmaceutical industry, MERCAPTO POLYETHYLENE GLYCOL 5,000 MONOMETHYL ETHER is used as a component in drug delivery systems. The hydrophilic PEG spacer improves the solubility and bioavailability of drugs, while the thiol group enables the formation of stable bonds with drug molecules or carriers, enhancing the overall performance of the drug delivery system.
Used in Surface Modification:
In materials science, MERCAPTO POLYETHYLENE GLYCOL 5,000 MONOMETHYL ETHER is used as a surface modification agent for transition metal surfaces, such as gold and silver. The thiol group can form strong bonds with these surfaces, allowing for the creation of functionalized surfaces with tailored properties, such as improved biocompatibility, enhanced catalytic activity, or targeted drug release.
Used in Diagnostics:
In the diagnostics industry, MERCAPTO POLYETHYLENE GLYCOL 5,000 MONOMETHYL ETHER is used as a component in the development of diagnostic tools and assays. The thiol group can be utilized to attach specific recognition elements, such as antibodies or oligonucleotides, to diagnostic platforms, enabling the detection and quantification of target molecules in biological samples.

Upstream product

• 62921-74-8 2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate 
• 72593-77-2 3,6,9-trioxadecyl bromide 
• 17356-08-0 thiourea 
• 112-35-6 triethylene glucol monomethyl ether 
• 857284-78-7 S-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)ethanethioate 
• 168640-82-2 11-azido-3,6,9-trioxa-undecanyl p-toluenesulfonate 
• 37860-51-8 tetraethylene glycol di(p-toluenesulfonate) 
• 1310827-26-9 S-2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl ethanethioate 
• 1347750-79-1 2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethanethiol 
• 112-60-7 Tetraethylene glycol 
• 50586-80-6 toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester 
• 111-77-3 2-(2-methoxyethoxy)ethyl alcohol 
• 62921-76-0 2,5,8,11-tetraoxatridecan-13-ol tosylate 
• 23783-42-8 tetraethylene glycol monomethyl ether 

Downstream Products

• 885476-31-3 C₁₃H₁₄N₂O₂S 
• 1266328-47-5 4,5-[2-(2-methoxyethoxy)ethylsulfanyl]phthalonitrile 
• 1452877-36-9 C₆₀H₁₀₂O₂₁S₃ 
• 1643575-07-8 [meso-5,10,15,20-tetrakis(4-[2-(2-methoxyethoxy)ethane]thioxytetra-2,3,5,6-fluorophenyl)porpholactonato]platinum(II) 
• 1229649-33-5 N-(4-((4-(3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureido)naphthalen-1-yloxy)methyl)pyridin-2-yl)-2-(2-(2-methoxyethoxy)ethylthio)acetamide 

Relevant articles and documents

Adsorbed surfactants for affinity chromatography: End-group modification of ethylene glycol polymers

The hydroxyl end-groups of PluronicF108 {a tri-block copolymer surfactant of poly(ethylene glycol) and poly(propylene glycol) [PEG-PPG-PEG]} were converted into primary amine and quaternary ammonium equivalents for use in a new approach to affinity chromatography. The preparation of sulphonic acid end-groups was also attempted.

Biofunctional silicon nanoparticles by means of thiol-ene click chemistry

The preparation and characterization of butylene-terminated silicon nanoparticles (SiNPs) and their functionalization using thiol-ene chemistry is described, as well as the coupling of DNA strands. Bromide-terminated SiNPs were prepared by means of the oxidation of magnesium silicide and functionalized with butylene chains through treatment with the corresponding Grignard reagent. The successful coupling was confirmed by NMR and FTIR spectroscopy. TEM measurements revealed a silicon-core diameter of (2.4±0.5)nm. The fluorescence emission maximum is at λmax=525nm when excited at λexc=430nm. The conjugation of these alkene-terminated SiNPs by means of thiol-ene chemistry is described for a variety of functional thiols. Efficient coupling was evidenced by NMR and FTIR spectroscopy. Moreover, the characteristic fluorescence properties of the SiNPs remained unaltered, thus demonstrating the value of this approach towards functional oxide-free SiNPs. Activation of the attached carboxylic acid moieties allowed for conjugation of NH2-terminated oligo-ssDNA (ss=single strand) to the SiNPs. Successful coupling was confirmed by a characteristic new UV absorption band at 260nm, and by the still-present distinctive fluorescence of the SiNPs at 525nm. Gel electrophoresis confirmed coupling of 2 to 3 DNA strands onto the SiNPs, whereas no uncoupled DNA was observed.

Lithium-Conducting Self-Assembled Organic Nanotubes

Supramolecular polymers are compelling platforms for the design of stimuli-responsive materials with emergent functions. Here, we report the assembly of an amphiphilic nanotube for Li-ion conduction that exhibits high ionic conductivity, mechanical integrity, electrochemical stability, and solution processability. Imine condensation of a pyridine-containing diamine with a triethylene glycol functionalized isophthalaldehyde yields pore-functionalized macrocycles. Atomic force microscopy, scanning electron microscopy, and in solvo X-ray diffraction reveal that macrocycle protonation during their mild synthesis drives assembly into high-aspect ratio (>103) nanotubes with three interior triethylene glycol groups. Electrochemical impedance spectroscopy demonstrates that lithiated nanotubes are efficient Li+ conductors, with an activation energy of 0.42 eV and a peak room temperature conductivity of 3.91 ± 0.38 × 10-5 S cm-1. 7Li NMR and Raman spectroscopy show that lithiation occurs exclusively within the nanotube interior and implicates the glycol groups in facilitating efficient Li+ transduction. Linear sweep voltammetry and galvanostatic lithium plating-stripping tests reveal that this nanotube-based electrolyte is stable over a wide potential range and supports long-term cyclability. These findings demonstrate how the coupling of synthetic design and supramolecular structural control can yield high-performance ionic transporters that are amenable to device-relevant fabrication, as well as the technological potential of chemically designed self-assembled nanotubes.

Solid phase synthesis of oligoethylene glycol-functionalized quinolinecarboxamide foldamers with enhanced solubility properties

A series of octameric quinoline oligoamide foldamers has been synthesized consisting exclusively of monomers which display mono-, di-, tri- or tetra-ethylene glycol side-chains. These oligomers adopt stable helical conformations. New Fmoc-acid monomer precursors were first developed. The microwave assisted solid-phase synthesis (SPS) methodology for oligomer preparation is described, and it is demonstrated that small adjustments in side-chain length translate into large differences in the solubility profile of the oligomers. The impact of such modifications on foldamer preparation, handedness inversion kinetics and potential applications is also discussed.