Bromo-PEG2-phosphonic acid

 CAS No.: 1446282-44-5  Cat No.: BP-501116 4.5  

Bromo-PEG2-phosphonic acid is a bifunctional PEG-based linker featuring a terminal alkyl bromide that acts as an electrophile in nucleophilic substitution and a phosphonic acid group that mainly contributes acidity, polarity, and coordination behavior. Structurally, it is a short ethylene glycol spacer (PEG2) that provides aqueous solubility and conformational flexibility while maintaining defined end-group reactivity. In PROTAC and targeted protein degradation design, such linkers are used to connect a ligand-bearing electrophile to a second module (for example, a nucleophile-functionalized ligand or other compatible partner), enabling controlled spatial positioning that can improve ternary complex formation and degradation efficiency. The phosphonic acid functionality can also support robust binding to metal-containing materials or facilitate salt-forming interactions that enhance handling and reproducibility. Overall, this reagent is valuable for researchers seeking reliable, water-compatible linker chemistry to tune linker length and attachment geometry in targeted degradation constructs.

Bromo-PEG2-phosphonic acid

Structure of 1446282-44-5

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PROTAC Linker
Molecular Formula
C₆H₁₄BrO₅P
Molecular Weight
277.05

* For research and manufacturing use only. Not for human or clinical use.

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IUPACName
2-[2-(2-bromoethoxy)ethoxy]ethylphosphonic acid
InChI Key
NKJZEERRSMGNLG-UHFFFAOYSA-N
InChI
InChI=1S/C6H14BrO5P/c7-1-2-11-3-4-12-5-6-13(8,9)10/h1-6H2,(H2,8,9,10)
SMILES
C(COCCBr)OCCP(=O)(O)O

Bromo-PEG2-phosphonic acid is a PEG-based, bromo-functional linker designed for constructing PROTACs through reliable covalent attachment handles while providing a hydrophilic, spacer-like segment that can improve solubility and molecular presentation. Its phosphonic acid functionality supports robust conjugation strategies and stable linker behavior in aqueous, biologically relevant environments. The structure and reactivity considerations for assembling PROTACs with this linker are described in detail below.

Structure: The linker combines a short poly(ethylene glycol) spacer with a terminal bromo group and a phosphonic acid moiety. It contains ether linkages within the PEG chain, a C–Br bond at the reactive terminus, and a phosphonate group capable of strong hydrogen bonding and metal/ion interactions, contributing to high aqueous compatibility.

Reactivity: The bromo handle is suited to nucleophilic substitution or related coupling approaches that install the linker onto amine, thiol, or other nucleophile-bearing warheads under standard organic synthesis conditions. The phosphonic acid group can participate in coupling workflows that require acid-activated intermediates or phosphonate-compatible activation chemistries. Typical solvent systems include polar organic/aqueous mixtures, with base and mild heating often used to promote substitution while maintaining functional-group integrity.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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