Nonaethylene glycol di(p-toluenesulfonate)
CAS No.: 109635-64-5
Cat No.: BP-500312
Purity: >95%
4.5 
Nonaethylene glycol di(p-toluenesulfonate) is a polyethylene glycol–based bifunctional linker bearing two terminal p-toluenesulfonate leaving groups, providing a flexible, hydrophilic chain length that spans nine ethylene glycol units. The sulfonate termini are well suited for nucleophilic substitution, enabling controlled conjugation to complementary nucleophiles (for example, amines or other suitable functional groups) on target-binding ligands and E3 ligase–recruiting moieties. In PROTAC architectures, such PEG linkers help tune the effective distance and relative orientation between the two binding domains, often improving productive ternary complex formation and thereby enhancing targeted protein ubiquitination and degradation efficiency. As a modular intermediate, this reagent supports rapid synthesis of PROTACs and related bifunctional degraders, allowing researchers to systematically vary linker length and polarity while maintaining robust, reproducible coupling chemistry.
Structure of 109635-64-5
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This Nonaethylene glycol di(p-toluenesulfonate) is a bifunctional, PEG-based linker designed to enable efficient coupling between targeting ligands and E3 ligase recruiters in PROTAC architectures. Its flexible ethylene glycol backbone supports favorable linker conformations and solubility, while the two activated tosylate termini provide reliable electrophilic handles for nucleophilic substitution. The following sections describe its structure and the practical reactivity considerations for PROTAC synthesis.
Structure: The linker consists of a repeating nonaethylene glycol chain terminated by two p-toluenesulfonate leaving groups. It features ether linkages along the PEG backbone and sulfonate ester functionalities at both ends. These components confer high polarity and good solubility in common organic solvents while maintaining chemical stability under non-nucleophilic conditions.
Reactivity: The tosylate termini participate in nucleophilic substitution reactions, enabling attachment to amines, thiols, or other nucleophiles typically used to form PROTAC conjugates. Coupling is commonly performed under anhydrous, inert conditions with suitable base to generate the nucleophile, using polar aprotic solvents to promote substitution. Mechanistically, displacement of the tosylate occurs via an SN2-type pathway when steric effects allow, producing stable ether or thioether/amine linkages depending on the nucleophile.
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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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