6-Bromohexylphosphonic acid
CAS No.: 133345-66-1
Cat No.: BP-501110
4.5 
6-Bromohexylphosphonic acid is a bifunctional linker bearing a terminal bromide for alkylation and a phosphonic acid group that contributes acidity, polarity, and coordination capability. Structurally, it provides a six-carbon spacer that positions the reactive bromide at a defined distance from the phosphonate, with the alkyl bromide serving as the main covalent reaction site for SN2 substitution by suitable nucleophiles. In PROTAC construction, such linkers are employed to connect a ligand-derived warhead to an E3-recruiting element while tuning geometry, flexibility, and local physicochemical properties that influence ternary complex formation and ubiquitination efficiency. Its phosphonic acid functionality can also contribute to altered polarity and hydrogen-bonding patterns at the linker–protein interface, which may improve degradation performance for certain target classes. Overall, this reagent is valuable for researchers seeking chemically robust, distance-controlled linker architectures to systematically optimize PROTAC activity.
Structure of 133345-66-1
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6-Bromohexylphosphonic acid is a functionalized phosphonic acid linker building block designed for constructing PROTACs through modular coupling to targeting ligands and E3-recruiting moieties. Its phosphonic acid functionality enables robust attachment chemistry while the bromohexyl handle provides a versatile electrophilic site for forming linker intermediates. This product supports the synthesis of targeted protein degraders by facilitating controlled assembly of degradation architectures; detailed structural and reactivity considerations are provided below.
Structure: The molecule contains a phosphonic acid group attached to a hexyl chain bearing a terminal bromide. It features P–C and C–Br bonds, with a strongly polar, hydrogen-bonding phosphonate motif that can exist in mono- or di-anionic forms depending on pH. The overall polarity supports solubility in suitable polar media.
Reactivity: The terminal bromide can participate in nucleophilic substitution to generate linkage intermediates for PROTAC assembly, typically via SN2-type displacement under conditions that favor backside attack. Suitable nucleophiles include oxygen, nitrogen, or sulfur nucleophiles derived from ligand-bearing functional groups. Phosphonic acids may require base-mediated activation or protection strategies to control chemoselectivity. Common approaches use polar aprotic solvents and bases compatible with phosphonate chemistry, with careful control of temperature and stoichiometry to minimize side reactions.
* 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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