Bromoacetamido-PEG8-acid

 CAS No.: 1698019-89-4  Cat No.: BP-501600  Purity: >95% 4.5  

Bromoacetamido-PEG8-acid is a polyethylene glycol linker bearing a terminal bromoacetamide electrophile and a carboxylic acid for convenient chemical handling. Structurally, it comprises an extended PEG chain (eight ethylene glycol units) that provides aqueous solubility and conformational spacing, while the bromoacetamide group enables selective covalent conjugation to nucleophilic residues such as cysteine thiols or primary amines under appropriate conditions. In PROTAC and targeted degradation designs, this linker functions as a modular spacer that connects two functional components—typically a ligand for an E3 ubiquitin ligase and a ligand for the target protein—by first installing the linker onto one partner through the reactive bromoacetamide handle and then using the terminal acid for subsequent coupling to the second component. The PEG8 length helps reduce steric interference at the ternary complex interface and can improve overall degradation efficiency by maintaining productive geometry and minimizing nonspecific interactions.

Bromoacetamido-PEG8-acid

Structure of 1698019-89-4

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Category
PROTAC Linker
Molecular Formula
C21H40BrNO11
Molecular Weight
562.45
Appearance
Pale Yellow Oily Liquid

* 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 Oily Liquid
Storage
Store at 2-8°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
3-[2-[2-[2-[2-[2-[2-[2-[2-[(2-bromoacetyl)amino]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
Synonyms
Bromoacetamido-PEG8-C2-acid; Bromoacetamido-PEG8-CH2CH2COOH; BrCH2CONH-PEG8-acid; 6,9,12,15,18,21,24,27-Octaoxa-3-azatriacontan-30-oic acid, 1-bromo-2-oxo-; 1-bromo-2-oxo-6,9,12,15,18,21,24,27-octaoxa-3-azatriacontan-30-oic acid
Boiling Point
671.3±55.0°C at 760 mmHg
Density
1.3±0.1 g/cm3
InChI Key
KLVSMPBQYRYTMJ-UHFFFAOYSA-N
InChI
InChI=1S/C21H40BrNO11/c22-19-20(24)23-2-4-28-6-8-30-10-12-32-14-16-34-18-17-33-15-13-31-11-9-29-7-5-27-3-1-21(25)26/h1-19H2,(H,23,24)(H,25,26)
SMILES
C(COCCOCCOCCOCCOCCOCCOCCOCCNC(=O)CBr)C(=O)O

Bromoacetamido-PEG8-acid is a polyethylene glycol-based bifunctional linker designed for modular construction of PROTACs, enabling efficient conjugation between a ligand and an E3-recruiting element while maintaining favorable solubility and conformational flexibility. Its reactive bromoacetamide handle supports targeted formation of stable linkages, which can improve synthetic accessibility and facilitate systematic structure–activity studies. The following sections describe its structure and the practical reactivity considerations for PROTAC assembly in detail below.

Structure: The molecule contains a PEG chain terminating in a carboxylic acid and a bromoacetamide electrophile. It features ether linkages within the PEG segment, an amide linkage at the bromoacetamide terminus, and a reactive carbon–bromine bond suitable for nucleophilic substitution, yielding a stable conjugation point.

Reactivity: The bromoacetamide group is suited to nucleophilic substitution with amines or other nucleophiles under conditions commonly used for alkylation, typically in polar organic solvents or aqueous/organic mixtures. Reaction proceeds via formation of a covalent bond through displacement of bromide, with the amide carbonyl providing an electrophile activated for selective conjugation. Base selection and pH control are often used to balance nucleophile availability and minimize side reactions during PROTAC synthesis.

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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

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