Bromoacetamido-PEG4-acid

 CAS No.: 1807518-67-7  Cat No.: BP-500627  Purity: ≥95% 4.5  

Bromoacetamido-PEG4-acid is a PEG-based PROTAC linker featuring a terminal bromoacetamide electrophile and a carboxylic acid for downstream conjugation. Structurally, it provides a flexible hydrophilic spacer of moderate length that can reduce steric interference between the two binding modules of a PROTAC while maintaining productive geometry for ternary complex formation. The bromoacetamide group is designed for chemoselective alkylation of nucleophilic residues, most commonly primary amines or thiols, enabling site-specific attachment to an appropriate ligand or warhead through stable C–N or C–S bond formation. In targeted protein degradation workflows, this linker architecture supports modular assembly of degraders by facilitating controlled conjugation chemistry and improving solubility and effective presentation of functional groups. Its carboxylic acid handle further supports coupling strategies for purification or bioconjugation, making it a practical building block for systematic structure–activity relationship studies in PROTAC design.

Bromoacetamido-PEG4-acid

Structure of 1807518-67-7

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Category
PROTAC Linker
Molecular Formula
C13H24BrNO7
Molecular Weight
386.24
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, DMSO, Water
Appearance
Pale Yellow or Colorless Oily Matter
ShelfLife
-20°C 3 years powder; -80°C 2 years in solvent
Storage
Store at 2-8°C
Shipping
Room temperature, or blue ice upon request.
IUPACName
3-[2-[2-[2-[2-[(2-bromoacetyl)amino]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
Synonyms
Bromoacetamido-PEG4-C2-acid; Bromoacetamido-PEG4-CH2CH2COOH; BrCH2CONH-PEG4-acid; 1-Bromo-2-oxo-6,9,12,15-tetraoxa-3-azaoctadecan-18-oic acid; Propanoic acid, 3-[(14-bromo-13-oxo-3,6,9-trioxa-12-azatetradec-1-yl)oxy]-; 6,9,12,15-Tetraoxa-3-azaoctadecan-18-oic acid, 1-bromo-2-oxo-
Boiling Point
557.7±50.0 °C at 760 mmHg
Density
1.4±0.1 g/cm3
InChI Key
LMFYGPXSVUULRZ-UHFFFAOYSA-N
InChI
InChI=1S/C13H24BrNO7/c14-11-12(16)15-2-4-20-6-8-22-10-9-21-7-5-19-3-1-13(17)18/h1-11H2,(H,15,16)(H,17,18)
SMILES
C(COCCOCCOCCOCCNC(=O)CBr)C(=O)O

Bromoacetamido-PEG4-acid, provides a PEG-based spacer terminating in a bromoacetamide handle and a carboxylic acid for conjugation. Its flexible, hydrophilic architecture can improve effective ternary complex formation by modulating linker length and solvation. The bromoacetamide motif enables chemoselective coupling to nucleophilic ligands, supporting robust assembly of targeted protein degraders. Detailed structural and reactivity considerations are provided below.

Structure: The linker comprises a polyethylene glycol segment connected to a bromoacetamide electrophile and a terminal carboxylic acid. It contains amide and ether linkages, with a reactive alkyl bromide adjacent to the carbonyl. The PEG chain confers water compatibility and conformational flexibility.

Reactivity: The bromoacetamide group is designed for nucleophilic substitution with suitable amine or thiol nucleophiles under conditions that favor amide formation and minimize hydrolysis. Typical coupling is performed in polar aprotic or mixed aqueous media, often using base to promote nucleophile deprotonation. No metal catalyst is generally required; the reaction proceeds via electrophilic alkylation followed by stable bond formation, yielding a functional PROTAC intermediate.

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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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