Bromo-PEG2-t-butyl acetate

 CAS No.: 1807518-63-3  Cat No.: BP-500643 4.5  

Bromo-PEG2-t-butyl acetate is a heterobifunctional polyethylene glycol linker featuring a terminal bromo group for electrophilic functionalization and a short PEG chain that provides aqueous solubility and conformational flexibility. The linker terminus is protected as a t-butyl acetate, which can serve as a chemically stable handle during synthesis and later be removed or transformed under appropriate conditions to reveal a reactive functionality for conjugation. In PROTAC design, PEG linkers are widely used to reduce steric clashes between the ligand-binding domains and to tune the effective distance and orientation required for productive ternary-complex formation. The bromo functionality enables attachment to nucleophilic groups on warheads or E3-ligase ligands via substitution or related coupling strategies, while the PEG segment helps maintain mobility of the conjugated moieties in physiological-like media. This product is valuable for constructing modular targeted degradation probes, facilitating rapid synthesis of linker variants and optimization of degradation potency and selectivity through systematic spacer engineering.

Bromo-PEG2-t-butyl acetate

Structure of 1807518-63-3

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Category
PROTAC Linker
Molecular Formula
C₁₀H₁₉BrO₄
Molecular Weight
283.16
Appearance
Liquid

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

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Appearance
Liquid
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
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Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl 2-[2-(2-bromoethoxy)ethoxy]acetate
Synonyms
Br-PEG2-CH2COOtBu; Bromo-PEG2-CH2COOtBu
InChI Key
LEOVLGAAQMGPBM-UHFFFAOYSA-N
InChI
InChI=1S/C10H19BrO4/c1-10(2,3)15-9(12)8-14-7-6-13-5-4-11/h4-8H2,1-3H3
SMILES
CC(C)(C)OC(=O)COCCOCCBr

Bromo-PEG2-t-butyl acetate is a PEG-based, bromo-functional linker designed for modular PROTAC assembly, enabling efficient conjugation between ligands and facilitating controlled spatial presentation for ternary-complex formation. Its ether-rich PEG segment supports solubility and conformational flexibility, while the bromo handle provides a practical electrophilic site for subsequent coupling steps. The t-butyl acetate motif offers an orthogonal protection/reactivity profile commonly leveraged in linker chemistry. The details below describe the structure and reactivity considerations for PROTAC construction.

Structure: The linker contains an ether-oxygen rich PEG segment providing flexibility and improved hydrophilicity, coupled to a bromo-bearing electrophilic terminus. A t-butyl acetate ester contributes a protected carbonyl functionality. Overall, it comprises ether and ester linkages with a reactive C–Br bond suitable for substitution chemistry.

Reactivity: The bromo terminus is suitable for nucleophilic substitution reactions used in PROTAC synthesis, typically under polar aprotic conditions with an appropriate base and nucleophile derived from the partner ligand. Ester-containing motifs such as t-butyl acetate are often handled under conditions that preserve the ester during coupling, with selective deprotection performed when needed. Reaction design should follow established electrophile–nucleophile pairing principles and be optimized for ligand stability.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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