BrCH2CONH-PEG3-COOtBu

 CAS No.: 1807537-33-2  Cat No.: BP-500665  Purity: ≥95% 4.5  

BrCH2CONH-PEG3-COOtBu is a bromomethyl amide–terminated polyethylene glycol linker designed for modular PROTAC synthesis. Structurally, it contains a PEG3 ethylene glycol chain that provides aqueous solubility and conformational flexibility, flanked by a reactive bromomethyl group and a protected carboxylate (tert-butyl ester) at the opposite end. The bromomethyl functionality enables efficient conjugation to nucleophilic partners (e.g., amines or other tethering motifs) through alkylation, while the carboxylate protection allows controlled downstream coupling after deprotection. In targeted protein degradation workflows, such PEG-based linkers help position the E3-ligand and target-binding warhead at an appropriate spatial distance and reduce unfavorable steric or electrostatic effects, thereby supporting productive ternary complex formation. This linker is valuable for researchers optimizing linker length and attachment chemistry to improve degradation potency, selectivity, and overall physicochemical properties of PROTAC constructs.

BrCH2CONH-PEG3-COOtBu

Structure of 1807537-33-2

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Category
PROTAC Linker
Molecular Formula
C15H28BrNO6
Molecular Weight
398.29
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 DMSO
Appearance
Pale Yellow or Colorless Oily Matter
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl 3-[2-[2-[2-[(2-bromoacetyl)amino]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
Bromoacetamido-PEG3-t-butyl ester; Bromoacetamido-PEG3-C2-Boc; tert-butyl 1-bromo-2-oxo-6,9,12-trioxa-3-azapentadecan-15-oate; 4,7,10-Trioxa-13-azapentadecanoic acid, 15-bromo-14-oxo-, 1,1-dimethylethyl ester; 2-Methyl-2-propanyl 1-bromo-2-oxo-6,9,12-trioxa-3-azapentadecan-15-oate; 6,9,12-Trioxa-3-azapentadecan-15-oic acid, 1-bromo-2-oxo-, 1,1-dimethylethyl ester
Boiling Point
507.6±50.0°C at 760 mmHg
Density
1.3±0.1 g/cm3
InChI Key
QAQLZWBWKHLATI-UHFFFAOYSA-N
InChI
InChI=1S/C15H28BrNO6/c1-15(2,3)23-14(19)4-6-20-8-10-22-11-9-21-7-5-17-13(18)12-16/h4-12H2,1-3H3,(H,17,18)
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCNC(=O)CBr

BrCH2CONH-PEG3-COOtBu, is designed to support efficient PROTAC assembly by providing a flexible hydrophilic spacer and a functional handle for conjugation to ligands. Its ether-rich chain improves solubility and conformational adaptability, which can enhance productive ternary complex formation. The protected carboxylate enables controlled downstream coupling, while the bromoacetamide motif offers a practical electrophilic site for stepwise construction.

Structure: The linker contains an ether-rich PEG segment that imparts flexibility and hydrophilicity, flanked by a bromoacetamide unit and a tert-butyl-protected carboxylate. It features amide and ether linkages, an alkyl bromide electrophile, and a protected ester functionality that can be selectively unmasked for coupling.

Reactivity: The bromoacetamide portion can participate in nucleophilic substitution reactions with amine or other nucleophiles under standard organic synthesis conditions, enabling ligand attachment. The tert-butyl ester is typically removed under acid-mediated deprotection to reveal a carboxylic acid for amide or related bond formation. Common coupling strategies employ activated carboxylic acid derivatives with appropriate bases and dry, inert solvents, using established peptide-coupling chemistries.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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