Bromoacetamido-C2-PEG2-NH-Boc

 CAS No.: 182244-33-3  Cat No.: BP-500851 4.5  

Bromoacetamido-C2-PEG2-NH-Boc is a bifunctional PEG-based linker featuring a bromoacetamide electrophile at one terminus and a protected amine (Boc) at the other, connected through a short ethylene spacer and a two-unit poly(ethylene glycol) segment. The bromoacetamide group is designed for chemoselective conjugation to nucleophilic residues such as thiols (e.g., cysteine-containing handles) via stable thioether formation, enabling efficient attachment of the linker to protein-binding or warhead-bearing molecules. The PEG spacer provides conformational flexibility and improved aqueous solubility, which can help maintain productive geometry for ternary complex formation in PROTAC constructs. In targeted protein degradation research, this linker is useful for assembling modular PROTACs by linking an electrophilic handle-bearing component to an amine-functionalized partner after deprotection, supporting systematic structure–activity studies and optimization of linker length and polarity.

Bromoacetamido-C2-PEG2-NH-Boc

Structure of 182244-33-3

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PROTAC Linker
Molecular Formula
C₁₃H₂₅BrN₂O₅
Molecular Weight
369.25

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

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IUPACName
tert-butyl N-[2-[2-[2-[(2-bromoacetyl)amino]ethoxy]ethoxy]ethyl]carbamate
InChI Key
BLSNVTJXXUWHQT-UHFFFAOYSA-N
InChI
InChI=1S/C13H25BrN2O5/c1-13(2,3)21-12(18)16-5-7-20-9-8-19-6-4-15-11(17)10-14/h4-10H2,1-3H3,(H,15,17)(H,16,18)
SMILES
CC(C)(C)OC(=O)NCCOCCOCCNC(=O)CBr

Bromoacetamido-C2-PEG2-NH-Boc, is designed to support efficient PROTAC assembly by providing a flexible hydrophilic spacer and a reactive electrophile for amide-forming conjugation. Its ether-rich chain improves solubility and can help tune linker length and conformational freedom between the ligand warheads. The subsequent points describe its structural features and practical reactivity considerations for constructing targeted protein degraders in a stepwise, research-focused workflow.

Structure: The linker contains a bromoacetamide electrophilic handle, a short alkyl spacer, and a PEG segment providing multiple ether linkages. It also includes protected amine functionality (Boc) and an acetamide carbonyl, enabling controlled coupling while maintaining chemical stability during intermediate steps.

Reactivity: The bromoacetamide group is suitable for nucleophilic substitution by amines under basic conditions, forming stable C–N bonds consistent with alkylation of activated bromoacetamides. The Boc-protected amine can be selectively deprotected using standard acid conditions to reveal a primary amine for subsequent coupling. Common approaches employ polar aprotic solvents and appropriate bases, with reaction monitoring by standard analytical methods to ensure selective conversion.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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