Diethyl 12-bromododecylphosphonate
CAS No.: 264231-28-9
Cat No.: BP-501594
4.5 
Diethyl 12-bromododecylphosphonate is a long-chain, alkyl bromide phosphonate building block featuring a diethyl phosphonate headgroup and a terminal bromide that serves as a versatile electrophile. The extended dodecyl spacer provides a hydrophobic, conformationally flexible linker region, while the phosphonate functionality enables robust chemical handle(s) for stepwise PROTAC assembly through nucleophilic substitution or related coupling strategies to connect phosphonate-containing fragments with other ligands. In targeted protein degradation designs, such linkers are used to tune the spatial relationship between the recruiting ligand (e.g., E3 ligase binder) and the target-binding moiety, thereby optimizing productive ternary complex formation and degradation efficiency. As a standardized phosphonate-based linker precursor, it is valuable for researchers developing degraders that require long-range reach, improved synthetic modularity, and controlled attachment chemistry for systematic structure–activity studies.
Structure of 264231-28-9
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Diethyl 12-bromododecylphosphonate, provides a chemically robust handle for building targeted protein degradation constructs through reliable carbon–phosphonate chemistry and alkyl bromide functionalization. Its long, flexible phosphonate-containing chain supports linker length tuning and can improve effective spatial positioning between ligand modules. The subsequent points describe its structural features and practical synthetic considerations for assembling PROTACs.
Structure: The linker is an alkyl bromide bearing a dialkyl phosphonate group, featuring a phosphonate P=O motif, P–O–ethyl bonds, and a C–Br leaving group on a saturated hydrocarbon chain. Its amphiphilic character and flexible alkyl backbone support conformational adaptability in bifunctional degraders.
Reactivity: The bromide enables nucleophilic substitution reactions to connect the linker to ligand-bearing nucleophiles (for example, amines or oxygen nucleophiles) under standard alkylation conditions. The phosphonate can participate in phosphonate-based coupling or further functionalization using established phosphonate chemistry. Typical approaches employ polar aprotic solvents, temperature-controlled conditions, and base or acid catalysts as appropriate to the nucleophile and electrophile, following conventional PROTAC linker assembly strategies.
* 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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