Diethyl 8-bromooctylphosphonate
CAS No.: 124939-70-4
Cat No.: BP-501033
4.5 
Diethyl 8-bromooctylphosphonate is a phosphonate ester bearing an eight-carbon bromoalkyl chain, providing a chemically versatile handle for PROTAC linker construction. Structurally, the phosphonate group offers a stable, polar linkage motif that can be retained under common organic synthesis conditions, while the terminal bromide acts as an electrophile in nucleophilic substitution with amines, thiols, alkoxides, or other suitable nucleophiles. In PROTAC design, such bromoalkyl phosphonate linkers are used to spatially tune the distance and relative orientation between the target-binding ligand and the E3 ligase-recruiting moiety, thereby influencing ternary complex formation and degradation efficiency. The phosphonate functionality can also contribute to altered solubility and conformational preferences compared with purely hydrocarbon linkers. As a result, this reagent is valuable for systematic linker optimization in targeted protein degradation research, supporting reproducible synthesis of conjugates for structure–activity relationship studies.
Structure of 124939-70-4
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Diethyl 8-bromooctylphosphonate is a versatile alkyl phosphonate linker building block used in PROTAC synthesis to connect targeting ligands to E3-recruiting or binding motifs via a reactive bromoalkyl handle. Its phosphonate core offers a robust, polar linkage that can support stable conjugation chemistries, while the terminal bromide enables efficient functionalization under standard organic synthesis conditions. Detailed structural and reaction considerations are provided below.
Structure: The molecule contains a diethyl phosphonate group attached to a flexible eight-carbon alkyl chain terminating in a bromide. It features P–O and P–C connectivity, with esterified phosphonate oxygen atoms and a primary bromide suitable for substitution. The overall structure combines polar phosphonate character with hydrophobic chain flexibility.
Reactivity: The brominated alkyl terminus is suitable for nucleophilic substitution reactions to install the linker into PROTAC scaffolds, typically via SN2-type pathways with appropriate nucleophiles. Common approaches employ base-activated alcohols, amines, or thiols in polar aprotic solvents, with temperature and stoichiometry tuned to minimize elimination and side reactions. Phosphonate esters generally remain compatible under mild conditions used for linker coupling, enabling subsequent PROTAC assembly steps.
* 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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