31521-83-2

Basic information

• Product Name: 2-[2-(2-methoxyethoxy)ethoxy]-ethanethiol
• Synonyms: 2-[2-(2-methoxyethoxy)ethoxy]-ethanethiol;2-Methoxy[2-ethoxy(2-ethoxy)]-1-ethanethiol;MPEG3-SH;m-PEG3-thiol;Thiol-PEG3-methyl
• CAS NO: 31521-83-2
• Molecular Formula: C₇H₁₆O₃S
• Molecular Weight: 180.27
• EINECS: -0
• Mol File: 31521-83-2.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 50 °C(Press: 1 Torr)
• Appearance: /
• Density: 1.017
• PKA: 9.65±0.10(Predicted)
• CAS DataBase Reference: 2-[2-(2-methoxyethoxy)ethoxy]-ethanethiol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[2-(2-methoxyethoxy)ethoxy]-ethanethiol(31521-83-2)
• EPA Substance Registry System: 2-[2-(2-methoxyethoxy)ethoxy]-ethanethiol(31521-83-2)

Safety Data

• Hazardous Substances Data: 31521-83-2(Hazardous Substances Data)

Usage

Synthesis

Toluene-4-sulfonic acid 2-[2-(2-methoxyethoxy)-ethoxy]-ethyl ester (2.7) (10.8 g, 34 mmol) and thiourea (2.6 g, 34 mmol) were dissolved in a mixture of absolute EtOH (20 mL) and H2O (14 mL) and the mixture was refluxed for 3h. 4N NaOH solution (10 mL) was added to mixture and the reaction mixture refluxed 2 more h. The reaction mixture was concentrated under reduced pressure to ~ 10 mL, diluted with distilled H2O (10 mL) and neutralized with concentrated HCl. The solution was extracted with CH2Cl2 (3x10mL) and the solvent was evaporated under reduced pressure. The pink-yellow liquid was distilled at 0.45 torr pressure. The product was collected as a clear liquid and obtained in 54% yield. B.p. 55-57 °C at 0.45 torr. GC-MS Calcd. C7H16O3S+ : 180.0; found: 179.9. 1 H NMR (250 MHz, CDCl3) δ 3.6(6H), 3.5(4H), 3.4(3H), 2.7(2H), 1.6(1H); 13 C NMR (300 MHz, CDCl3) δ 76.92, 73.30, 72.34, 70.98, 70.63, 59.46, 24.66

Upstream product

• 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 
• 72593-77-2 3,6,9-trioxadecyl bromide 
• 17356-08-0 thiourea 
• 62921-74-8 2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate 
• 857284-78-7 S-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)ethanethioate 
• 112-35-6 triethylene glucol monomethyl ether 

Downstream Products

• 314263-25-7 4-(2-(2-(2-methoxyethoxy)ethoxy)ethylthio)phthalonitrile 
• 1345865-67-9 C₃₃H₅₂O₆SSi₄ 
• 1452877-36-9 C₆₀H₁₀₂O₂₁S₃ 
• 314263-26-8 4,5-bis(4′,7′,10′-trioxaundecylsulfanyl)phthalonitrile 
• 623-25-6 p-Xylylene dichloride 

Relevant articles and documents

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.

Improved methodology for the preparation of water-soluble maleimide-functionalized small gold nanoparticles

Improved methodology to prepare maleimide-functionalized, water-soluble, small (3 nm) gold nanoparticles using a retro-Diels-Alder strategy that we developed for similar organic-soluble AuNP's is described. Importantly, our results suggest that a recent paper by Zhu, Waengler, Lennox, and Schirrmacher describing a similar strategy gave results inconsistent with the formation of the titled maleimide-modified AuNP (Zhu, J.; Waengler, C.; Lennox, R. B.; Schirrmacher, R. Langmuir2012, 28, 5508) as the major product, but consistent with the major product being an adduct derived from the hydrolysis of maleimide formed under the conditions used for the required deprotection of the maleimide. Our methodology provides an efficient and accessible route to pure maleimide-modified small AuNP's that circumvents the formation of the hydrolysis product. The maleimide-modified small AuNP's are versatile because they are soluble in water and in a wide range of organic solvents and their reactivity can now be properly exploited as a reactive moiety in Michael addition for bioconjugation studies in aqueous solution.