2-(2-hydroxyethoxy)ethyl 4-methylbenzenesulfonate
CAS No.: 118591-58-5
Cat No.: BP-500455
4.5 
2-(2-hydroxyethoxy)ethyl 4-methylbenzenesulfonate is a sulfonate ester featuring a tosyl (p-toluenesulfonyl) leaving group linked to a short, flexible 2-(2-hydroxyethoxy)ethyl chain. Structurally, it provides a reliable electrophilic sulfonate functionality that can be used to convert alcohol-containing intermediates into activated derivatives under standard organic synthesis conditions. In PROTAC construction, such activated sulfonates are commonly employed as linkers or as functional handles to enable efficient conjugation between the ligand-bearing fragments, for example by facilitating nucleophilic substitution or controlled coupling to hydroxylated or other nucleophile-bearing moieties. The short ethylene glycol–like segment contributes flexibility and can help tune solubility and effective reach between the target-binding and E3-recruiting components. This reagent is therefore valuable for researchers developing targeted protein degradation molecules that require robust, reproducible linker installation and modular assembly of bifunctional constructs.
Structure of 118591-58-5
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2-(2-hydroxyethoxy)ethyl 4-methylbenzenesulfonate, is designed to enable efficient formation of ether-linked conjugates used in targeted protein degradation workflows. Its sulfonate leaving group supports reliable nucleophilic substitution, while the hydroxyethoxyethyl segment provides a hydrophilic, flexible handle that can improve solubility and linker presentation. The following sections describe its structure and practical reactivity considerations in PROTAC assembly.
Structure: The linker contains a benzenesulfonate ester functionality attached to a hydroxyethoxyethyl chain. It features aromatic sulfonyl substitution, an ether-containing aliphatic segment, and an alcohol-bearing motif that can support hydrogen bonding. Overall, it combines a good leaving group with a flexible, polar tether.
Reactivity: The sulfonate ester is suited for nucleophilic substitution with alcohol or amine nucleophiles under base-promoted conditions, typically in polar aprotic or mixed solvent systems compatible with PROTAC synthesis. Mechanistically, the sulfonate group acts as an effective leaving group, enabling formation of new C–O or C–N linkages. Mild bases and controlled stoichiometry are commonly used to minimize side reactions such as hydrolysis, and reaction progress is monitored by standard analytical methods.
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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