Bromo-PEG5-t-butyl ester

 CAS No.: 1415800-38-2  Cat No.: BP-501046  Purity: ≥95% 4.5  

Bromo-PEG5-t-butyl ester is a heterobifunctional polyethylene glycol linker featuring a terminal bromo leaving group and a PEG chain of five ethylene glycol units capped as a tert-butyl ester. Structurally, the bromo terminus enables controlled attachment to nucleophilic handles on ligands (for example, via substitution with thiols or amines after appropriate activation), while the PEG spacer provides water solubility and conformational flexibility that can reduce steric interference between the two PROTAC partners. The tert-butyl ester serves as a protected carboxylate equivalent, allowing subsequent deprotection or coupling to introduce the functional group required for amide or ester bond formation during PROTAC assembly. In targeted protein degradation workflows, such PEG-based linkers help tune effective intramolecular geometry, improve handling of conjugates, and support modular synthesis of degraders by providing orthogonal reactive sites. This makes the reagent valuable for constructing PROTACs and related bifunctional degraders with reproducible conjugation chemistry.

Bromo-PEG5-t-butyl ester

Structure of 1415800-38-2

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Category
PROTAC Linker
Molecular Formula
C17H33BrO7
Molecular Weight
429.34
Appearance
Pale Yellow or Colorless Oily Matter

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

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Purity
≥95%
Solubility
Soluble in DCM, DMF, DMSO
Appearance
Pale Yellow or Colorless Oily Matter
Storage
Store at 2-8°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl 3-[2-[2-[2-[2-(2-bromoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
Br-PEG5-COOtBu; Br-PEG5-CH2CH2COOtBu; Bromo-PEG5-C2-Boc; tert-butyl 1-bromo-3,6,9,12,15-pentaoxaoctadecan-18-oate; 4,7,10,13,16-Pentaoxaoctadecanoic acid, 18-bromo-, 1,1-dimethylethyl ester; 2-Methyl-2-propanyl 1-bromo-3,6,9,12,15-pentaoxaoctadecan-18-oate; 3,6,9,12,15-Pentaoxaoctadecan-18-oic acid, 1-bromo-, 1,1-dimethylethyl ester
Boiling Point
453.9±40.0 °C at 760 mmHg
Density
1.2±0.1 g/cm3
InChI Key
CFAPOEDUPYZKFH-UHFFFAOYSA-N
InChI
InChI=1S/C17H33BrO7/c1-17(2,3)25-16(19)4-6-20-8-10-22-12-14-24-15-13-23-11-9-21-7-5-18/h4-15H2,1-3H3
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCOCCOCCBr

Bromo-PEG5-t-butyl ester is a functionalized PEG-based linker designed for modular construction of PROTACs, enabling efficient conjugation between a ligand-bearing warhead and an E3-recruiting moiety. Its ether-rich PEG segment supports favorable solubility and conformational flexibility, while the bromo handle provides a chemically addressable site for subsequent derivatization. The t-butyl ester offers a protected carboxyl functionality that can be unmasked under suitable conditions during linker assembly. Detailed structural and reactivity considerations are provided below.

Structure: The linker comprises an ether-containing polyethylene glycol chain terminated with a bromo substituent and a t-butyl ester group. It features C–Br and ester carbonyl functionalities connected through stable C–O and C–C bonds, providing a flexible, polar scaffold with enhanced hydrophilicity.

Reactivity: The bromo group is suitable for nucleophilic substitution or related electrophile-driven coupling to install a second fragment under standard organic synthesis conditions. The t-butyl ester can be selectively deprotected using acid-mediated cleavage to reveal a carboxylic acid for subsequent amide or ester bond formation. Solvent choice and base/acid strength should be optimized to preserve sensitive ligands and maintain linker integrity.

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* 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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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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