Tetraethylene glycol dimethyl ether - CAS 143-24-8

Me-PEG4-Me is a polyethylene glycol (PEG)-based PROTAC linker. Me-PEG4-Me can be used in the synthesis of a series of PROTACs.

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Molecular Formula
C10H22O5
Molecular Weight
222.28

Tetraethylene glycol dimethyl ether

    • Specification
      • Purity
        98%
        Appearance
        Transparent Liquid
        Storage
        4°C, sealed storage, away from moisture; In solvent, -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)
        Shipping
        Room temperature in continental US; may vary elsewhere.
        IUPAC Name
        1-methoxy-2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethane
        Synonyms
        Tetraglyme; Dimethoxytetraglycol
    • Properties
      • Boiling Point
        275.3±0.0 °C at 760 mmHg
        Melting Point
        -30°C
        Density
        1.009
        InChI Key
        ZUHZGEOKBKGPSW-UHFFFAOYSA-N
        InChI
        InChI=1S/C10H22O5/c1-11-3-5-13-7-9-15-10-8-14-6-4-12-2/h3-10H2,1-2H3
        Canonical SMILES
        COCCOCCOCCOCCOC
    • Reference Reading
      • 1. The Power of Stoichiometry: Conditioning and Speciation of MgCl2/AlCl3 in Tetraethylene Glycol Dimethyl Ether-Based Electrolytes
        Georg Bieker, Michael Salama, Martin Kolek, Yossef Gofer, Peter Bieker, Doron Aurbach, Martin Winter ACS Appl Mater Interfaces. 2019 Jul 10;11(27):24057-24066.doi: 10.1021/acsami.9b05307.Epub 2019 Jun 26.
        In many Mg-based battery systems, the reversibility of Mg deposition and dissolution is lowered by parasitic formation processes of the electrolyte. Therefore, high Coulombic efficiencies of Mg deposition and dissolution are only achieved after several "conditioning" cycles. As this phenomenon is especially reported for AlCl3-containing solutions, this study focuses on the "conditioning" mechanisms of MgCl2/AlCl3 and MgHMDS2/AlCl3 (HMDS = hexamethyldisilazide) in tetraethylene glycol dimethyl ether (TEGDME)-based electrolytes. Electrochemical (cyclic voltammetry) and spectroscopic investigations (27Al nuclear magnetic resonance spectroscopy, Raman spectroscopy, inductively coupled plasma optical emission spectroscopy, scanning electron microscopy, and energy-dispersive X-ray spectroscopy) reveal that cationic AlCl2+ species in TEGDME-based electrolytes with an AlCl3/MgCl2 ratio higher than 1:1 corrode the Mg metal. According to a cementation reaction mechanism, the corrosion of Mg is accompanied with Al deposition. In effect, the consumption of Mg results in low Coulombic efficiencies of Mg deposition and dissolution during the electrolyte "conditioning". After understanding the mechanism of this process, we demonstrate that a careful adjustment of the stoichiometry in MgCl2/AlCl3 and MgHMDS2/AlCl3 in TEGDME formulations prevents Mg corrosion and results in "conditioning"-free, highly efficient Mg deposition and dissolution.
        2. Insights into the Structure and Dynamics of Imidazolium Ionic Liquid and Tetraethylene Glycol Dimethyl Ether Cosolvent Mixtures: A Molecular Dynamics Approach
        Qianjin Guo, Qiang Liu, Yixin Zhao Nanomaterials (Basel). 2021 Sep 27;11(10):2512.doi: 10.3390/nano11102512.
        In this work, the effect of molecular cosolvents tetraethylene glycol dimethyl ether (TEGDME) on the structure and versatile nature of mixtures of these compounds with imidazolium-based ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6]) is analyzed and discussed at a molecular level by means of all-atom molecular dynamics (MD) simulations. In the whole concentration range of the binary mixtures, the structures and properties evolution was studied by means of systematic molecular dynamics simulations of the fraction of hydrogen bonds, the radial and spatial distribution functions for the various molecular ions and molecular species in the system, together with the snapshots visualization of equilibrated simulation boxes with a color-coding scheme and the rotational dynamics of coumarin 153 (C153) in the binary mixtures. The goal of the work is to provide a molecular-level understanding of significant improvement of ionic conductivity and self-diffusion with the presence of TEGDME as a cosolvent, which causes an enhancement to the ion translational motion and fluidity in the [bmim][PF6] ionic liquids (ILs). Under a mixture concentration change, the microstructure changes of [bmim][PF6] with the TEGDME molar fraction (XTEG) above 0.50 show a slight difference from that of neat [bmim][PF6] IL and concentrated [bmim][PF6]/TEGDME mixture in terms of the radial and spatial distribution functions. The relative diffusivities of solvent molecules to cations as a function of concentration were found to depend on the solvent but not on the anion. A TEGDME increase is found to be advantageous to the dissipation of the polar regions as well as the nonpolar regions in the [bmim][PF6] ionic liquids. These conclusions are consistent with the experimental results, which verified that the unique, complex, and versatile nature of [bmim][PF6]/TEGDME mixture can be correctly modeled and discussed at a molecular level using MD simulation data.
        3. Combining activated carbon adsorption with heterogeneous photocatalytic oxidation: lack of synergy for biologically treated greywater and tetraethylene glycol dimethyl ether
        Holger Gulyas, Angel Santiago Oria Argáez, Fanzhuo Kong, Carlos Liriano Jorge, Susanne Eggers, Ralf Otterpohl Environ Technol. 2013 May-Jun;34(9-12):1393-403.doi: 10.1080/09593330.2012.751129.
        The aim of the study was to evaluate whether the addition of activated carbon in the photocatalytic oxidation of biologically pretreated greywater and of a polar aliphatic compound gives synergy, as previously demonstrated with phenol. Photocatalytic oxidation kinetics were recorded with fivefold concentrated biologically pretreated greywater and with aqueous tetraethylene glycol dimethyl ether solutions using a UV lamp and the photocatalyst TiO2 P25 in the presence and the absence of powdered activated carbon. The synergy factor, SF, was quantified as the ratio of photocatalytic oxidation rate constant in the presence of powdered activated carbon to the rate constant without activated carbon. No synergy was observed for the greywater concentrate (SF approximately 1). For the aliphatic compound, tetraethylene glycol dimethyl ether, addition of activated carbon actually had an inhibiting effect on photocatalysis (SF < 1), while synergy was confirmed in reference experiments using aqueous phenol solutions. The absence of synergy for the greywater concentrate can be explained by low adsorbability of its organic constituents by activated carbon. Inhibition of the photocatalytic oxidation of tetraethylene glycol dimethyl ether by addition of powdered activated carbon was attributed to shading of the photocatalyst by the activated carbon particles. It was assumed that synergy in the hybrid process was limited to aromatic organics. Regardless of the lack of synergy in the case of biologically pretreated greywater, the addition of powdered activated carbon is advantageous since, due to additional adsorptive removal of organics, photocatalytic oxidation resulted in a 60% lower organic concentration when activated carbon was present after the same UV irradiation time.
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