Tetraethylene glycol bis(p-toluenesulfonate) - CAS 37860-51-8

Tetraethylene glycol bis(p-toluenesulfonate) is a polyethylene glycol (PEG)-based PROTAC linker that can be used in the synthesis of a series of PROTACs.

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Molecular Formula
C22H30O9S2
Molecular Weight
502.60

Tetraethylene glycol bis(p-toluenesulfonate)

    • Specification
      • Purity
        >95%
        Solubility
        10 mM in DMSO
        Appearance
        Colorless to Yellow Clear Liquid
        Storage
        Store at 2-8°C
        Shipping
        Room temperature in continental US; may vary elsewhere
        IUPAC Name
        2-[2-[2-[2-(4-methylphenyl)sulfonyloxyethoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate
        Synonyms
        Tos-PEG5-Tos; Tos-PEG4-Tos; ((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) bis(4-Methylbenzenesulfonate); Tetraethylene glycol ditosylate; Tetraethylene Glycol Di-p-tosylate; Tetraethylene Glycol Bis(p-toluenesulfonate); 2,2'-(Ethylenedioxy)triethyl ditosylate; 1,11-Bis(tosyloxy)-3,6,9-trioxaundecane; Bis[2-(2-tosyloxyethoxy)ethyl] Ether; Bis[2-[2-(p-toluenesulfonyloxy)ethoxy]ethyl] Ether; Ethanol, 2,2'-[oxybis(2,1-ethanediyloxy)]bis-, bis(4-methylbenzenesulfonate)
    • Properties
      • Boiling Point
        635.0±55.0°C (Predicted)
        Melting Point
        65-69°C
        Density
        1.242 g/mL at 25°C
        InChI Key
        SLAONPBUWDUSSO-UHFFFAOYSA-N
        InChI
        InChI=1S/C22H30O9S2/c1-19-3-7-21(8-4-19)32(23,24)30-17-15-28-13-11-27-12-14-29-16-18-31-33(25,26)22-9-5-20(2)6-10-22/h3-10H,11-18H2,1-2H3
        Canonical SMILES
        CC1=CC=C(C=C1)S(=O)(=O)OCCOCCOCCOCCOS(=O)(=O)C2=CC=C(C=C2)C
    • Reference Reading
      • 1. Functionalized fluorescent terephthalate monomers and their attempted polyester formation
        Yvonne S L Choo, Marta Giamberini, José Antonio, Paul G Waddell, Andrew C Benniston Org Biomol Chem. 2020 Nov 4;18(42):8735-8745. doi: 10.1039/d0ob01533d.
        The reaction of diethyl 2,5-bis(tert-butyl)phenoxy-3,6-dihydroxyterephthalate (1) with tetraethylene glycol di(p-toluenesulfonate) under high-dilution conditions afforded several isolated products. Two products were identified as macrocycles with one being the 1 + 1 crown ether derivative 3 (10% yield), and the second being the 2 + 2 crown ether compound D3 (19% yield). The X-ray structure for 3 was determined with the asymmetric unit observed to comprise half of the molecule. The small crown ether ring of 3 interacts with K+ or H+ ions in MeOH, but binding is weak and the macrocyclic cavity is too small to fully encapsulate the K+ ion. Transesterification of compounds 1, its methylated version 2 and 3 with diols such as ethylene glycol or 1,4-butandiol produced monomers (M1-M3) which were reacted with terephthaloyl chloride. Short oligomers were produced (PolyM1-PolyM3) rather than extensive polymeric materials and all displayed solid state fluorescence. The absorption and fluorescence properties of M1-M2 and their polymers can be related to subtle structural changes. The Stokes shift for M2 of 15 627 cm-1 in DCM is one of the largest observed for a simple organic chromophore in fluid solution.
Bio Calculators
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L

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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